Field of the Invention:
The present invention relates to solid state forms of 5-fluoro-3-phenyl-2-[(IS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-], represented by the following structural formula:
The present invention also relates to solid state forms of salts of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1.
The present invention further relates to improved process for the preparation of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quina2olin-4(3H)-one compound of formula-1.

Background of the Invention:
Several compounds have been identified as PI3K inhibitors. For example, compounds capable of inhibiting the biological activity of human P.I3K, including 5-ftuoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one, and their uses are disclosed in U.S. Patent No. 6,518,277, U.S. Patent No. 6,667,300, and U.S. Patent No. 7,932,260.
5-Fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one known as Idelalisib. In July 2014, ZYDELIG (Idelalisib), a first-in-class inhibitor of POK delta, was approved by the U.S. Food and Drug Administration for the treatment of three B-cell blood cancers.
ZYDELIG has also been approved by the European Commission for two blood cancers, chronic lymphocytic leukemia (CLL) and follicular lymphoma (PL),
International (PCT) Publication No. WO2005/113556 Al discloses quinazolones as

inhibitors of phosphoinositide 3-kinase (PI3K) delta and provides preparation of Idelalisib and related compounds but does not discuss about its polymorphic form.
International (PCT) Publication No. WO20I3/134288 Al discloses various crystalline forms of Idelalisib, Form I, Form II, Form III, Form IV, Form V, Form VI and Form VII.
International (PCT) Publication No. WO2015/0I43I5 AI discloses various crystalline polymorphic forms of Idelalisib, Form II, Form III, Form IV, Form V (THF solvate), Form VI (tetrahydrate), Form VII (tert-butyl ether solvate), Form VIII, Form IX and Form X (dioxane solvate).
International (PCT) Publication No. WO20I5/095605 Al discloses hydrochloric acid salt of Idelalisib and its polymorphic forms.
IPCOM000244272D publication discloses the crystalline forms of Idelalisib hydrochloric acid salt.

Brief description of the Invention:
The first aspect of the present invention is to provide a crystalline hydrobromide salt of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la, herein after designated as form-M and process for its preparation.
The second aspect of the present invention is to provide acid addition salts of 5-fluoro-3-phenyl-2-[(1S)-1-(9H-purin-6-ylamino)propyl]quinazof in-4(3 H)-one compound of formula-1.
The third aspect of the present invention is to provide a process for the preparation of acid addition salts of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-yl amino)propyl] quinazolin-4(3H)-one compound of formula-1.
The fourth aspect of the present invention relates to novel crystalline form of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1, herein after designated as form-N and process for its preparation.
The fifth aspect of the present invention is to provide a process for the preparation
of 5-fluoro-3-phenyl-2-[(IS)-l-(9H-purin-6-ylamino)propyl]quina2olin-4(3H)-one
compound of formula-1.

Brief description of the Drawings:
Figure 1: Illustrates the PXRD pattern of crystalline form-M of hydrobromide salt of 5-
fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound
of formula-la.
Figure 2: Illustrates the PXRD pattern of crystalline form-N of 5-fluoro-3-phenyl-2-[(l S)-
l-(9H-purin-6-yIamino)propyl]quinazolin-4(3H)-one compound of formula-I.
Figure 3: Illustrates the PXRD pattern of amorphous form of 5-fluoro-3-phenyl-2-[(lS)-l-
(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula- h
Figure 4: Illustrates the PXRD pattern of crystalline form-M of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-I.
Detailed description of the Invention:
Polymorphism, the occurrence of different crystal forms, is a property of some molecules and molecular complexes. A single molecule may give rise to a variety of polymorphs having distinct crystal structures and physical properties like melting point, thermal behaviors (e.g. measured by thermogravimetric analysis - "TGA", or differential scanning calorimetry - "DSC"), X-ray powder diffraction (XRPD or powder XRD) pattern, infrared absorption fingerprint, and solid state nuclear magnetic resonance (NMR) spectrum. One or more of these techniques may be used to distinguish different polymorphic forms of a compound.
Different salts and solid state forms of an active pharmaceutical ingredient may possess different properties. Such variations in the properties of different salts and solid state forms may provide a basis for improving formulation, for example, by facilitating better processing or handling characteristics, improving the dissolution profile, or improving stability and shelf-life. These variations in the properties of different salts and solid state forms may also provide improvements to the final dosage form, for instance, if they serve to improve bioavailability. Different salts and solid state forms of an active pharmaceutical ingredient may also give rise to a variety of polymorphs or crystalline forms, which may in turn provide additional opportunities to assess variations in the properties and characteristics of a solid active pharmaceutical ingredient.
Discovering new salts and solid state forms of a pharmaceutical product can provide materials having desirable processing properties, such as ease of handling, ease of processing, storage stability, and ease of purification or as desirable intermediate crystal

forms that facilitate conversion to other polymorphic forms. New salts and solid state forms of a pharmaceutically useful compound can also provide an opportunity to improve the performance characteristics of a pharmaceutical product. It enlarges the repertoire of materials that a formulation scientist has available for formulation optimization, for example by providing a product with different properties, e.g., better processing or handling characteristics, or improved shelf-life. For at least these reasons, there is a need for additional salts and solid state forms of Idelalisib; in particular there is a need for salts and solid state forms that have improved solubility.
As used herein the term "suitable solvent" used in the present invention refers to "hydrocarbon solvents" such as n-hexane, n-heptane, cyclohexane, pet ether, toluene, pentane, cycloheptane, methyl cyclohexane, m-, o-, or p-xylene, and the like; "ether solvents" such as dimethoxy methane, tetrahydrofuran, 1,3-dioxane, 1,4-dioxane, furan, diethyl ether, ethylene glycol dimethyl ether, ethylene glycol diethyl ether, diethylene glycol dimethyl ether, diethylene glycol diethyl ether, triethylene glycol dimethyl ether, anisole, t-butyl methyl ether, 1,2-dimethoxy ethane and the like; "ester solvents" such as methyl acetate, ethyl acetate, isopropyl acetate, n-butyl acetate and the like; "polar-aprotic solvents such as dimethylacetamide (DMA), dimethylformamide (DMF), dimethyl sulfoxide (DMSO), N-methylpyrrolidone (NMP) and the like; "chloro solvents" such as dichloro methane, dichloroethane, chloroform, carbon tetrachloride and the like; "ketone solvents" such as acetone, methyl ethyl ketone, methyl isobutylketone and the like; "nitrile solvents" such as acetonitrile, propionitrile, isobutyronitrile and the like; "alcoholic solvents" such as methanol, ethanol, n-propanol, isopropanol, n-butanol, isobutanol, t-butanol, 2-nitroethanol, 2-fluoroethanol, 2,2,2-trifluoroethanol, ethylene glycol, 2-methoxyethanol, I, 2-ethoxyethanol, diethylene glycol, 1, 2, or 3-pentanol, neo-pentyl alcohol, t-pentyl alcohol, diethylene glycol monoethyl ether, cyclohexanol, benzyl alcohol, phenol, or glycerol and the like; "polar solvents" such as water or mixtures thereof.
The term "suitable base" used herein the present invention until unless specified is selected from inorganic bases like "alkali metal hydroxides" such as lithium hydroxide, sodium hydroxide, potassium hydroxide and the like; "alkali metal carbonates" such as sodium carbonate, potassium carbonate, lithium carbonate and the like; "alkali metal bicarbonates" such as sodium bicarbonate, potassium bicarbonate, lithium bicarbonate and the like; "alkali metal hydrides" such as sodium hydride, potassium hydride, lithium
5

hydride and the like; "alkali metal alkoxides" such as sodium methoxide, sodium ethoxide,
sodium tert-butoxide, potassium methoxide, potassium ethoxide, potassium tert-butoxide
and the like; ammonia; and organic bases such as triethyl amine, methyl amine, ethyl
amine, l,8-Diazabicyc!o[5.4.0]undec-7-ene (DBU), l,5-Diazabicyclo(4.3.0)non-5-ene
(DBN), lithium diisopropylamide (LDA), n-butyl lithium, tribenzylamine, isopropyl
amine, diisopropylamine, diisopropylethylamine, N-methylmorpholine, N-ethyl
morpholine, piperidine, dimethylaminopyridine, morpholine, 2,6-lutidine, 2,4,6-collidine.
imidazole, l-methylimida2ole,-l32,4-triazole,-l-,4-diaEabicyclo[-272.2]octane (DABCO)or
mixtures thereof.
i
The suitable hydrochloric acid source is selected from HCI gas, aqueous HCI; dry
HC1, ethyl acetate-HCl, IPA-HC1, ethanol-HCl, methanol-HCl.
The first aspect of the present invention provides a crystalline form-M of hydro bromide salt of 5-fluoro-3-phenyl-2-[(lS)-I-(9H-purin-6-ylamino)propyl]quinazolin-4 (3H)-one compound of formula-la, characterized by its powder x-ray diffraction pattern having peaks at 9.4, 11.3, 12.3, 14.6, 15.1, 16.7, 16.8, 17.1, 17.5, 18.4, 18.6, 18.9, 19.4, 19.9, 20.4, 21.0, 21.5, 21.7, 22.9, 23.4, 23.7, 24.1, 24.3, 24.8, 25.1, 25.5, 26.7, 27.6, 28.1.
. 28.7, 29.1, 29.3, 29.7, 30.1, 31.2, 31.4, 33.3, 34.5 and 36.4 ±0.2 degrees two theta.
I
The crystalline form-M of hydrobromide salt of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-
purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la is characterized
by P-XRD pattern as depicted in figure-1.
Further, the crystalline form-M of hydrobromide salt of 5-fluoro-3-phenyl-2-[(lS)-
l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la is useful in-the preparation of pure free base of Idelalisib compound of formula-1.
Further, the present invention provides a process for the preparation of crystalline I form-M of hydro bromide salt of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-la, comprising of the following steps:
a) Adding a suitable solvent to 5-fluoro-3-phenyl-2-[(IS)-l-(9H-purin-6-ylamino)
propyl]quinazolin-4(3H)-one,
b) adding aqueous hydrobromide to the reaction mixture,
c) stirring the reaction mixture,

d) filtering the precipitated solid to provide crystalline form-M of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la.
Wherein, in step-a) the suitable solvent is selected from alcohol solvents such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol.
The preferred embodiment of the present invention provides a process for the preparation of crystalline form-M of hydrobromidc salt of 5-fluoro-3-phcnyl-2-[(lS>l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la, comprising of the following steps:
a) Adding isopropanol to 5-fluoro-3-phenyl-2-[(IS)-l-(9H-purin-6-ylamino)propyl] quinazolin-4(3H)-one,
b) adding hydrobromide to the reaction mixture,
c) stirring the reaction mixture,
d) filtering the precipitated solid to provide crystalline form-M of hydrobromide salt of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la.
The second aspect of the present invention provides acid addition salts of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1.
Wherein, the acid addition salts are selected from inorganic acids, such as hydro bromic acid, hydrochloric acid, sulfuric acid, nitric acid or phosphoric acid; and organic acids, such as oxalic acid, maleic acid, malonic acid, tartaric acid, fumaric acid, citric acid, malic acid, succinic acid, mandelic acid, lactic acid, acetic acid, propionic acid, 2-chloromandelate, p-toluene sulfonic acid, ethane-1,2-disulfonic acid, camphor sulfonic acid, ethane sulfonic acid, methane sulfonic acid, naphthalene-2-sulfonic acid, benzene sulfonic acid, adipic acid, glutaric acid, glutamic acid, palmitic acid or aspartic acid.
In another embodiment of the present invention encompasses the above acid addition salts and solid state forms of Idelalisib useful in the preparation of pure Idelalisib free base compound of formula-1.
The third aspect of the present invention provides a process for the preparation of

acid addition salts of 5-fluoro-3-phenyl-2-[(lS)-!-(9H-purin-6-ylamino)propyl] quinazolin-4(3H)-one compound of formula-], comprising of the following steps:
a) Adding a suitable solvent to 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-y!amino) propyl]quinazolin-4(3H)-one,
b) adding a suitable acid to the reaction mixture,
c) stirring the reaction mixture,
d) filtering the precipitated solid to provide acid addition salts of 5-fluoro-3-phenyl-
2-[(lS)-l-(9H-purin-6-yIamino)propyl]quinazolin-4(3H)-one compound of
formula-1.
Wherein,
In step-a) the suitable solvent is selected from alcohol solvents, chloro solvents, ketone
solvents, ester solvents, hydrocarbon solvents, ether solvents, polar aprotic solvents, nitrile
solvents, polar solvents like water or mixture thereof.
in step-b) the suitable acid is same as defined in the first aspect of the present invention.
Further, the acid addition salts of Idelalisib can be converted into highly pure Idelalisib free base compound of formula-l, by treating acid addition salts of Idelalisib with a suitable base.
The fourth aspect of the present invention provides novel crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1, characterized by its powder x-ray diffraction pattern having peaks at 8.7, 11.1, 11.7, 12.5, 13.4, 14.4, 14.6, 15.6, 16.2, 16.7, 17.7, 18.3, 18.5, 19.8,20.5,21.0,21.8, 22.1, 23.2, 23.7, 24.3, 25.2, 26.3, 27.3, 27.8, 31.8, 32.8, 33.5, 34.5 and 37.8.±0.2 degrees two theta.
The crystalline form-N of 5-fluoro-3-phenyl-2-[(1S)-1 -(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-1 is characterized by P-XRD pattern as depicted in figure-2.
Further, the crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-yl amino)propyl]quinazolin-4(3H)-one compound of formula-1 is useful in the preparation of pure Idelalisib compound of formula-1.

Further, the present invention provides a process for the preparation of crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1, comprising of the following steps:
a) Adding 5-fluoro-3-phenyl-2-[( 1S)-1 -(9H-purin-6-ylamino)propyl]quinazolin-4 (3H)-one to a suitable ester solvent such as methyl acetate, ethyl acetate, propyl acetate, butyl acetate, isopropyl acetate,
b) stirring the reaction mixture,
c) filtering the precipitated solid.to.get the.crystalline_form=N-of_5=nuoro=3-phen.y.l
2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4 (3H)-one compound of formula-1.
The preferred embodiment of the present invention provides a process for the preparation of crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-1, comprising of the following steps:
a) Adding ethyl acetate to 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl] quinazolin-4 (3H)-one,
b) stirring the reaction mixture,
c) filtering the precipitated solid to get the crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4 (3H)-one compound of formula-1.
Wherein, the crystalline form-N of 5-fluoro-3-phenyl-2-[(IS)-l-(9H-purin-6-yl amino)propyl]quinazolin-4(3H)-one compound of formula-1 is an ethyl acetate solvate.
The fifth aspect of the present invention provides a process for the preparation of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1, comprising of the following steps:
a) Reacting 2-fluoro-6-nitrobenzoic acid compound of formula-2 with a suitable chlorinating agent in a suitable solvent to provide acid chloride derivative compound of formula-2, which further reacts with aniline in presence of a suitable base in a suitable solvent to provide 2-fluoro-6-nitro-N-phenylbenzamide compound of formuIa-3,
b) reducing the compound of formula-3 with a suitable reducing agent in a suitable solvent to provide 2-amino-6-fluoro-N-phenylbenzamide compound of formula-4,
9

c) coupling the compound of formula-4 with (S)-2-(tert-butoxycarbonylamino) butanoic acid compound of formula-5 in the presence of a suitable coupling agent in a suitable solvent to provide (S)-tert-butyl(l-((3-fluoro-2-(phenylcarbamoyl) phenyl)amino)-l-oxobutan-2-ylcarbamate compound of formula-6,
d) reacting the compound of formula-6 with a suitable base in presence of iodine in a suitable solvent to provide Boc-protected (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquinazolin-4 (3H)-one, which on further treating with a suitable acid in a suitable solvent followed by treating with a suitable base in a suitable solvent to provide (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one compound offormula-7,
e) reacting the compound of formula-7 with 6-halo-7H-purine compound of general formula-8 in presence of a suitable base in a suitable solvent to provide 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1,
f) optionally, treating the compound of formula-1 with a suitable acid to provide acid addition salts of compound of formula-1, which on further treating with a suitable base to provide pure 5-fluoro-3-phenyl-2-[(]S)-l-(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-1.
Wherein,
In step-a) the suitable chlorinating agent is selected from thionyl chloride (SOCb).
phosphorous pentachloride (PCIs), phosphorous oxychloride (POCb), oxalyl chloride,
gaseous hydrochloric acid; suitable base is selected from inorganic or organic base;
in step-b) the suitable reducing agent is selected from Fe, Fe in acidic media like NH4CI,
ammonium acetate or HCI or acetic acid, Sn in acidic media like HCI, Zn dust, Zn in
acidic media like HCI or NH4CI, ammonium acetate or acetic acid, stannous chloride
(SnCb), NaBH4, LiAlFLj, LiBHj, diborane, borane-THF complex, hydrazine hydrate,
hydrogenation catalysts such as Rhodium, sulfides, alkali metal dithionite, alkali metal
dithionate and sodium amalgam;
in step-c) the suitable coupling agent is selected from (DCC) N,N-dicyclohexyl
carbodimide, N,N'-diisopropylcarbodiimide, N-di-tert-butyl carbodiimide, 1,3-di-p-tolyl
carbodiimide, bis(3-chloro-2-methylphenyl)carbodiimide, bis(o-tolylcarbodiimide). l-tert-
butyl-3-ethylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbodiimide, bis(2,6-

diisopropylphenyl)carbodiimide, bis(2,6-diethylphenyl)carbodiimide, N-cyclohexyl-N'-
isopropylcarbodiimide, N-methyl-N'-phenylcarbodiimide, l-cyclohexyl-3-(2-(4-
morpholinyl)ethyl)carbodiimide, N3N'-dicyclohexyl-N-methylcarbodiimidium iodide, I-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (EDC-HCI), ((O-benzo triazol-l-yO-N^N'jN'-tetramethyluroniumtetrafluoroborate) (TBTU), 2-chloro-4,6-dimethoxy-l,3,5-triazine (CDMT), 2-chloro-l,3-dimethylimidazolium chloride (DMC), alkyl chloroformate compounds (e.g. ethyl chloroformate, isobutyl chloroformate (IBCf), or the like) and optionally, in addition to the coupling agent, a catalytic auxiliary nucleophile may be used to activate the carboxyl group. Suitable catalytic auxiliary nucleophiles which can be used to promote the reaction include, but are not limited to 1-hydroxybenzotriazole (HOBt), N-hydroxysuccinimede (HOSu) and N-hydroxy-5-norbene-endo-2,3-dicarboxamide (HONB);
in step-d) the suitable base is selected from inorganic, organic or organo metallic base such as lithium diisopropylamide, magnesium isopropyl amide, zinc isopropylamide, butyl zinc, butyl magnesium, hexamethyldisilazane (HMDS), LiHMDS, NaHMDS, Magnesium HMDS;
in step-e) the suitable base is selected from organic or inorganic base; in step-f) the suitable acid is same as defined in first aspect of the present invention and suitable base is selected from inorganic or organic base;
in step-d) the suitable acid is selected from hydrochloric acid in acetic acid, acetic acid in ethyl acetate, trifluoroacetic acid, HC1 gas, aqueous HCI, dry HC1, ethyl acetate-HCt, IPA-HC1, ethanol-HCI, methanol-HCl and suitable base is selected from organic or inorganic base;
in step-a) to step-f) the suitable solvent is selected from alcohol solvents, chloro solvents, ketone solvents, ester solvents, hydrocarbon solvents, ether solvents, polar aprotic solvents, nitrile solvents, polar solvents like water or mixture thereof.
The preferred embodiment of the present invention provides a process for the preparation of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4 (3H)-one compound of formula-1, comprising of the following steps:
a) Reacting 2-fluoro-6-nitrobenzoic acid compound of formula-2 with thionyl chloride in toluene to provide acid chloride derivative compound of formula-2, which further reacts with aniline in presence of triethyl amine in a mixture of

toluene and dimethyl formamide to provide 2-fluoro-6-nitro-N-phenylbenzamide compound of formula-3,
b) reducing the compound of formuIa-3 with iron and ammonium chloride in a mixture of methanol and water to provide 2-arnino-6-fluoro-N-phenylbenzamide compound of formula-4,
c) coupling the compound of formula-4 with (S)-2-(tert-butoxycarbonylamino) butanoic acid compound of formu!a-5 in presence of N,N-dicyclohexyl carbodimide (DCC) and 1-hydroxybenzotriazole (HOBt) in dichloromethane to provide (S)-tert-butyl (1 -((3-fluoro-2-(phenylcarbamoyl) phenyl)amino)-1 -oxobutan-2-ylcarbamate compound of formula-6,
d) reacting the compound of formula-6 with a hexamethyldisilazane (HMDS) and iodine in toluene to provide Boc-protected (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquinazolin-4 (3H)-one, which on further treating with ethyl acetate-HCI in isopropanol followed by treating with aqueous sodium carbonate in a mixture of water and ethyl acetate to provide (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquinazolin-4 (3H)-one compound of formula-7,
e) reacting the compound of formula-7 with 6-chloro-7H-purine compound of formula-8a in presence of diisopropylethyl amine in n-butanol to provide 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1,
f) optionally, treating the compound of formula-1 with a suitable acid to provide acid addition salts of compound of formula-1, which on further treating with a suitable base to provide pure 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-1.
5-fluoro-3-phenyl-2-[(lS)-I-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1 produced by the present invention can be further micronized or milled in a conventional techniques to get the desired particle size to achieve desired solubility profile based on different forms of pharmaceutical composition requirements. Techniques that may be used for particle size reduction include, but not limited to ball, roller and hammer mills, and jet mills. Milling or micronization may be performed before drying, or after the completion of drying of the product.
5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one

compound of formula-1 used in the present invention is prepared according to any of the
process known in the art. -The invention also encompasses pharmaceutical compositions comprising
compound of formula-1 or salts thereof of the present invention. As used herein, the term
"pharmaceutical compositions" or "pharmaceutical formulations" include tablets, pills,
powders, liquids, suspensions, emulsions, granules, capsules, suppositories, or injection
preparations.

Method of Analysis
PXRD analysis of compounds produced by the present invention were carried out using BRUKER D8 ADVANCE/AXS X-Ray diffractometer using Cu Ka radiation of wavelength 1.5406 A° and continuous scan speed of 0.03°/min.
The process of the present invention is schematically represented as below:

The process described in the present invention was demonstrated in examples illustrated below. These examples are provided as illustration only and therefore should not be construed as limitation of the scope of the invention.
Examples:
Examplc-1:
Preparation of crystalline form-M of hydrobromide sail of 5-fluoro-3-phenyl-2-|(lS)-
l-(9H-purin-6-yl amino)propyl]quinazolin-4(3H)-one: (Formula-la)
Isopropanol (50.0 ml) was added to 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-yl amino)propyl]quinazolin-4(3H)-one (5.0 gms) at 25-30°C. Aqueous hydrobromic acid solution (3.75 ml) was added to the reaction mixture at 25-30°C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with isopropanol and dried to get the title compound. Yield: 5.5 gms.
The P-XRD pattern of the obtained compound was depicted in figure-1. Example-2: Preparation of 2-fluoro-6-nitro-N-phenylbenzamide: (FormuIa-3)
Toluene (500 ml) and Dimethylformamide (10 ml) were added to 2-fluoro-6-nitrobenzoic acid (100 gms) compound of formula-2 at 25-30°C under nitrogen atmosphere. Thionyl chloride (118.2 ml) was added to the reaction mixture at 25-30°C. Heated the reaction mixture to 70-75°C and stirred for 4 hours at the same temperature. Distilled off the solvent from the reaction mixture under reduced pressure. Cooled the reaction mixture to 25-30°C. Toluene (300 ml) was added to the reaction mixture at 25-30°C. Toluene (300 ml) and Dimethylformamide (50 ml) were added to aniline (54.6 gms) at 25-30°C. Triethyl amine (227.7 ml) was added to the reaction mixture at 25-30°C. Cooled the reaction mixture to 0-5°C. Slowly added the obtained acid chloride solution to the reaction mixture at 0-5°C under nitrogen atmosphere. Raised the temperature of reaction mixture to 25-30°C and stirred for 3 hours at the same temperature. Water was added to the reaction mixture at 25-30°C and stirred for 3 hours at the same temperature. Filtered the precipitated solid, washed with water and dried to get the title compound. Yield: 190 gms. Example-3: Preparation of 2-Amino-6-fIuoro-N-phcnylbenzamide: (Formula-4)

Methanol (700 ml) was added to the obtained compound in example-2 at 25-30°C, Iron powder (121.1 gms) and followed by aqueous ammonium chloride solution (173.6 gms of ammonium chloride in 700 ml of water) was added to the reaction mixture at 25-30°C. Heated the reaction mixture to 65-70°C and stirred for 3 hours at the same temperature. Cooled the reaction mixture to 40-45°C. Ethyl acetate and water were added to the reaction mixture at 40-45°C and stirred for 20 minutes at the same temperature. Filtered the reaction mixture through hyflow bed and washed with ethyl acetate. Both the organic and aqueous layers were separated and aqueous layer was extracted with ethyl acetate. Combined the organic layers and washed with aqueous sodium chloride solution. Distilled off the solvent from the organic layer under reduced pressure. Ethyl acetate (50 ml) and cyclohexane (750 ml) were added to the obtained compound at 25-30°C. Heated the reaction mixture to 55-60°C and stirred for 45 minutes at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 3 hours at the same temperature. Filtered the precipitated solid, washed with cyclohexane and dried to get the title compound.
Yield: 95 gms; M.R: 1I4-116°C. Example-4:
Preparation of (S)-tert-butyl (l-((3-fluoro-2-(phenylcarbamoyl)phenyl)amino)-l-oxo butan-2-ylcarbamate: (Formula-6)
Dichloromethane (2000 ml) was added to 2-amino-6-fluoro-N-phenylbenzamide (200 gms) at 25-30°C under nitrogen atmosphere. (S)-2-((tert-butoxycarbonyl)amino) butanoic acid (353.7 gms) and followed by hydroxybenzotriazole (23.98 gms) was added to the reaction mixture at 25-30°C. Cooled the reaction mixture to 10-15°C. A mixture of N.N'-dicyclohexyl carbodiimide (358.1 gms) and dichloromethane (1000 ml) was slowly added to the reaction mixture at 10-15°C. Raised the temperature of the reaction mixture to 25-30°C and stirred for 10 hours at the same temperature. Filtered the reaction mixture and washed with dichloromethane. Water was added to the obtained filtrate at 25-30°C and stirred for 30 minutes at the same temperature. Both the organic and aqueous layers were separated and organic layer was washed with aqueous sodium carbonate solution and followed by aqueous sodium chloride solution. Distilled off the solvent from the organic layer under reduced pressure. Methyl tert-butyl ether (1000 ml) was added to the obtained compound at 25-30°C. Heated the reaction mixture to 50-55°C and stirred for 45 minutes at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 2 hours at

the same temperature. Filtered the precipitated solid, washed with methyl tert-butyl ether
and dried to get the title compound.
Yield: 345 gms; MR: 165-172°C.
Example-5:
Preparation of (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquinazolin-4(3H)-one:
(Formula-7)
Toluene (2.25 Its) was added to (S)-tert-butyl (l-((3-fluoro-2-(phenylcarbamoyl) phenyl)amino)-I-oxobutan-2-ylcarbamatc (225.0 gms) at 25-30°C under nitrogen atmosphere. Hexamethyldisilazane (261.4 gms) was added to the reaction mixture at 25-30°C. Iodine (275.1 gms) was slowly added to the reaction mixture at 25-30°C. Heated the reaction mixture to 45-50°C and stirred for 10 hours at the same temperature. Cooled the reaction mixture to 25-30°C. 15% aqueous sodium thiosulfate solution was added to the reaction mixture at 25-30°C. Ethyl acetate was added to the reaction mixture at 25-30°C and stirred for 30 minutes at the same temperature. Aqueous sodium carbonate solution was added to the reaction mixture at 25-30°C. Both the organic and aqueous layers were separated and the aqueous layer was extracted with ethyl acetate. Combined the organic layers and washed with 10% aqueous sodium chloride solution. Distilled off the solvent completely from organic layer under reduced pressure. Isopropanol (337.5 ml) was added to the obtained compound at 25-30°C and stirred for 15 minutes at the same temperature. Ethyl acetate-hydrochloric acid solution (337.5 ml) was added to the reaction mixture at 25-30°C and stirred for 40 minutes at the same temperature. Cooled the reaction mixture to 0-5°C and stirred for 3 hours at the same temperature. Filtered the precipitated solid and washed with pre-cooled mixture of isopropanol and ethyl acetate. To the obtained wet compound, water (1.12 Its) was added at 25-30°C. 20 % aqueous sodium carbonate solution was added to the reaction mixture at 25-30°C. Ethyl acetate (1.12 Its) was added to the reaction mixture at 25-30°C and stirred for 20 minutes at the same temperature. Both the organic and aqueous layers were separated and aqueous layer was extracted with ethyl acetate. Combined the organic layers and washed with 10% aqueous sodium chloride solution. Distilled off the solvent completely from the organic layer under reduced pressure. Ethyl acetate (135.0 ml) and cyclohexane (315.0 ml) were added to the obtained compound at 25-30°C and stirred for 2 hours at the same temperature. Filtered the solid, washed with cyclohexane and dried to get the title compound. Yield: 110 gms; M.R: 160-165°C.

Example-6:
Preparation of amorphous form of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)
propyl]quinazoIin-4(3H)-one: (Formula-1)
6-Chloropurine (42.8 gms) and n-butanol (750 ml) was added to (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquiriazolin-4(3H)-one (75.0 gms) at 25-30°C. N,N*-diiso propylethylamine (97.8 gms) was added to the reaction mixture at 25-30°C. Heated the reaction mixture to 95-100°C and stirred for 24 hours at the same temperature. Distilled off the solvent from the reaction mixture under reduced pressure. Methanol (150 ml) was added to the reaction mixture at 50-55°C. Cooled the reaction mixture to 25-30°C. The reaction mixture was slowly added to water (1500 ml) at25-30°C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with water and dried to get the title compound. Yield: 100 gms; Purity by HPLC: 85.61%.
Acetonitrile (450 ml) was added to the obtained compound at 25-30°C and stirred for 2 hours at the same temperature. Filtered the solid, washed with acetonitrile and dried to get the title compound. Yield: 62 gms; Purity by HPLC: 92.72%.
To the obtained solid, isopropanol (375 ml) was added at 25-30°C. Heated the reaction mixture to 75-80°C and stirred for 45 minutes at the same temperature. Carbon (7.5 gms) was added to the reaction mixture at 75-80°C and stirred for 30 minutes at the same temperature. Filtered the reaction mixture through hy-flow bed and washed with isopropanol. To the obtained filtrate, aqueous hydrobromide solution (45.0 ml) was added at 25-30°C and stirred for 3 hours at the same temperature. Filtered the precipitated solid and washed with isopropanol. Purity by HPLC: 99.45% The P-XRD pattern of the obtained compound was depicted in figure-1.
To the obtained compound, isopropanol (375 ml) was added at 25-30°C. Heated the reaction mixture to 75-80°C and stirred for 45 minutes at the same temperature. Cooled the reaction mixture to 25-30°C and stirred for 3 hours at the same temperature. Filtered the precipitated solid and washed with isopropanol. 10% aqueous sodium carbonate solution and ethyl acetate was added to the obtained compound at 25-30°C and stirred for 15 minutes at the same temperature. Both the organic and aqueous layers were separated and aqueous layer was extracted with ethyl acetate. Combined the organic layers

and washed with 10% aqueous sodium chloride solution. Distilled off the solvent
completely from the organic layer under reduced pressure. Methanol (750 ml) was added
to the reaction mixture at 40-45°C and stirred for 10 minutes at the same temperature.
Distilled off the solvent from the reaction mixture completely under reduced pressure.
Water was added to the reaction mixture at 25-30°C and stirred for 3 hours at the same
temperature. Filtered the reaction mixture and washed with water. Purity by HPLC:
99.96%.
The P-XRD pattern of the obtained compound was depicted in figur^-l.
Example-7:
Preparation of crystalline form-M of 5-fluoro-3-phenyl-2-|(lS)-l-(9H-purin-6-yl
amino)propyl]quinazolin-4(3H)-one: (Formula-1)
Acetonitrile was added to the obtained compound in example-6 at 25-30°C and stirred for 2 hours at the same temperature. Filtered the solid, washed with acetonitrile and dried to get the title compound. Yield: 36 gms; Purity by HPLC: 99.97%.
The P-XRD pattern of the obtained compound was depicted in Figure-4. Example-7:
Preparation of crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-yl amino)propyl]quinazolin-4(3H)-one: (Formula-1)
Ethyl acetate (6.0 ml) was added to 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-yl amino)propyl]quinazolin-4(3H)-one (1.0 gms) at 25-30°C and stirred for 2 hours at the same temperature. Filtered the precipitated solid, washed with isopropanol and dried to get the title compound. Yield: 0.7 gms. The P-XRD pattern of the obtained compound was depicted in figure-2.

We Claim:
1. A process for the preparation of 5-fluoro-3-phenyl-2-[(IS)-l-(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-1, comprising of the following steps: a) Reacting 2-fluoro-6-nitrobenzoic acid compound of formula-2
with a suitable chlorinating agent in a suitable solvent to provide acid chloride derivative compound of formula-2, which further reacts with aniline in presence of a suitable base in a suitable solvent to provide 2-fluoro-6-nitro-N-phenylbenzamide compound of formula-3,
b) reducing the compound of formula-3 with a suitable reducing agent in a suitable solvent to provide 2-amino-6-fluoro-N-phenylbenzamide compound of formula-4,
c) coupling the compound of formula-4 with (S)-2-(tert-butoxycarbonylamino) butanoic acid compound of formula-5
in the presence of a suitable coupling agent in a suitable solvent to provide (S)-tert-

butyl (l-((3-fluoro-2-(phenylcarbamoyl)phenyl)amino)-l-oxobutan-2-ylcarbamate compound of formula-6,
d) reacting the compound of formula-6 with a suitable base in presence of iodine in a suitable solvent to provide Boc-protected (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquinazolin-4 (3H)-one compound of formula-7, which on further treating with a suitable acid in a suitable solvent followed by treating with a suitable base in a suitable solvent to provide (S)-2-(l-aminopropyl)-5-fluoro-3-phenyl quinazolin-4(3H)-one compound of formula-7,
e) reacting the compound of formula-7 with 6-halo-7H-purine compound of general formula-8
in presence of a suitable base in a suitable solvent to provide 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1,

f) optionally, treating the compound of formula-] witfra'suitableacid td~pTovicle"acid addition salts of compound of formula-13 which on further treating with a suitable base to provide pure 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-y!amino)propyl] quinazolin-4(3H)-one compound of formula-l.
The process according to claim-1, wherein,
In step-a) the suitable chlorinating agent is selected from thionyl chloride (SOCb), phosphorous pentachloride (PCI5), phosphorous oxychloride (POCI3), oxalyl chloride, gaseous hydrochloric acid; suitable base is selected from inorganic or organic base; in step-b) the suitable reducing agent is selected from Fe, Fe in acidic media like NH4CI, ammonium acetate or HO or acetic acid, Sn in acidic media like HCI, Zn dust, Zn in acidic media like HCI or NH4CI, ammonium acetate or acetic acid, stannous chloride (SnCb), NaBH4, LiAIH4, UBH4, diborane, borane-THF complex, hydrazine hydrate, hydrogenation catalysts such as Rhodium, sulfides, alkali metal dithionite, alkali metal dithionate and sodium amalgam;
in step-c) the suitable coupling agent is selected from (DCC) N,N-dicyclohexyl
carbodimide, N,N'-diisopropylcarbodiimide, N-di-tert-butyl carbodiimide, 1,3-di-p-
tolylcarbodiimide, bis(3-chloro-2-methylphenyl)carbodiimide, bis(o-tolylcarbo
diimide), l-tert-butyl-3-ethylcarbodiimide, N-(3-dimethylaminopropyl)-N'-ethylcarbo
diimide, bis(2,6-diisopropylphenyl)carbodiimide, bis(2,6-diethylphenyl)carbodiimide,
N-cyclo hexyl-N'-isopropylcarbodiimide, N-methyl-N'-phenylcarbodiimide, 1-cyclo
hexyl-3-(2-(4-morpholinyl)ethy!)carbodiimide, N,N'-dicyclohexyl-N-methylcarbo
diimidium iodide, l-ethyl-3-(3-dimethy!aminopropyl)carbodiimide hydrochloride (EDC-HC1), ((O-benzotriazoi-l-yO-N^.N^N'-tetramethyluroniumtetrafluoroborate) (TBTU), 2-chloro-4,6-dimethoxy-l,3,5-triazine (CDMT), 2-chloro-l,3-dimethyl imidazotium chloride (DMC), alkyl chloroformate compounds (e.g. ethylchloro

formate, isobutyl chloroformate (IBCf), or the like) and suitable catalytic auxiliary nucleophiles is selected from 1-hydroxybenzotriazole (HOBt), N-hydroxysuccinimede (HOSu) and N-hydroxy-5-norbene-endo-2,3-dicarboxamide (HONB); in step-d) the suitable base is selected from inorganic, organic or organo metallic base such as lithium diisopropylamide, magnesium isopropyl amide, zinc isopropylamide. butyl zinc, butyl magnesium, hexamethyldisilazane (HMDS), LiHMDS, NaHMDS, Magnesium HMDS;
- in step-e) the suitable base-is-selected-fronvorganic or inorganic base;
in step-f) the suitable acid is selected from organic or inorganic acid and suitable base
is selected from inorganic or organic base;
in step-d) the suitable acid is selected from hydrochloric acid in acetic acid, acetic acid
in ethyl acetate, trifluoroacetic acid, HCI gas, aqueous HCl, dry HCI, ethyl acetate-
HCI, IPA-HC1, ethanol-HCl, methanol-HCI and suitable base is selected from organic
or inorganic base;
in step-a) to step-f) the suitable solvent is selected from alcohol solvents, chloro
solvents, ketone solvents, ester solvents, hydrocarbon solvents, ether solvents, polar
aprotic solvents, nitrile solvents, polar solvents like water or mixture thereof. _
3. A process for the preparation of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-1, comprising of the following steps:
a) Reacting 2-fluoro-6-nitrobenzoic acid compound of formula-2 with thionyl chloride in toluene to provide acid chloride derivative compound of formula-2, which further reacts with aniline in presence of triethyl amine in a mixture of toluene and dimethyl formamide to provide 2-fluoro-6-nitro-N-phenylbenzamide compound of formula-3,
b) reducing the compound of formula-3 with iron and ammonium chloride in a mixture of methanol and water to provide 2-amino-6-fluoro-N-phenylbenzamide compound of formula-4,
c) coupling the compound of formula-4 with (S)-2-(tert-butoxycarbonylamino) butanoic acid compound of formula-5 in presence of N,N-dicyclohexyl carbodimide (DCC) and 1-hydroxybenzotriazole (HOBt) in dichloromethane to

provide (S)-tert-butyl (l-((3-fluoro-2-(phenylcarbamoyl)phenyl)amino)-l-oxo butan-2-yIcarbamate compound of formula-6,
d) reacting the compound of formula-6 with a hexamethyldisilazane (HMDS) and iodine in toluene to provide Boc-protected (S)-2-(l-aminopropyl)-5-fluoro-3-phenylquinazolin-4 (3H)-one compound of formula-7, which on further treating with ethyl acetate-HCl in isopropanol followed by treating with aqueous sodium carbonate in a mixture of water and ethyl acetate to provide (S)-2-(l-aminopropyl)-5-fluoro-3-phcnylquinazolin-4 (3ll)-onc compound of formula-7,
e) reacting the compound of formula-7 with 6-chloro-7H-purine compound of formula-8a in presence of diisopropylethyl amine in n-butanol to provide 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1,
f) optionally, treating the compound of formula-1 with a suitable acid to provide acid addition salts of compound of formula-1, which on further treating with a suitable base to provide pure 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino) propyl]quinazolin-4(3H)-one compound of formula-1.
Crystalline form-M of hydro bromide salt of 5-fiuoro-3-phenyl-2-[( IS)-1 -(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la, characterized by its powder x-ray diffraction pattern having peaks at 9.4, 11.3, 12.3, 14.6, 15.1, 16.7, 16.8, 17.1, 17.5, 18.4, 18.6, 18.9, 19.4, 19.9, 20.4, 21.0, 21.5, 21.7, 22.9, 23.4, 23.7, 24.1, 24.3, 24.8, 25.1, 25.5, 26.7, 27.6, 28.1, 28.7, 29.1, 29.3, 29.7, 30.1, 31.2, 31.4, 33.3, 34.5 and 36.4 ±0.2 degrees two theta as depicted in figure-1.
A process for the preparation of crystalline form-M of hydrobromide salt of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la, comprising of the following steps:
a) Adding a suitable alcohol solvent to 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-yl amino)propyl]quinazolin-4(3H)-one,
b) adding aqueous hydrobormide to the reaction mixture,
c) stirring the reaction mixture,
d) filtering the precipitated solid to provide crystalline form-M of hydrobromide salt
23

of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la.
A process for the preparation of crystalline form-M of hydrobromide salt of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la, comprising of the following steps:
a) Adding isopropanol to 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]
- quinazolin-4(3H)-one, adding hydrobromide to the reaction mixture,
b) stirring the reaction mixture,
c) filtering the precipitated solid to provide crystalline form-M of hydrobromide salt of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-la.
Crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl] quinazolin-4(3H)-one compound of formula-1, characterized by its powder x-ray diffraction pattern having peaks at 8.7, 11.1, 11.7, 12.5, 13.4, 14.4, 14.6, 15.6, 16.2,
16.7, 17.7, 18.3, 18.5, 19.8, 20.5, 21.0, 21.8, 22.1, 23.2, 23.7, 24.3, 25.2, 26.3, 27.3,
27.7, 31.8, 32.8, 33.5, 34.5 and 37.8.±0.2 degrees two theta.
Acid addition salts of 5-fluoro-3-phenyl-2-[( 1 S)-l -(9H-purin-6-ylamino)propyl] quinazolin-4(3H)-one compound of formula-1, wherein, the suitable acid is selected from inorganic acids, such as sulfuric acid, nitric acid; and organic acids, such as oxalic acid, maleic acid, malonic acid, tartaric acid, fumaric acid, citric acid, malic acid, succinic acid, mandelic acid, lactic acid, acetic

acid, propionic acid, 2-chloromandelate, p-toluene sulfonic acid, ethane-l,2-disulfonic acid, camphor sulfonic acid, ethane sulfonic acid, methane sulfonic acid, naphthalene-2-sulfonic acid, benzene sulfonic acid, adipic acid, glutaric acid, glutamic acid, palmitic acid or aspartic acid.
A process for the preparation of crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1, comprising of the following step3:
a) Adding 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4 (3H)-one to a suitable ester solvents such as methyl acetate, ethyl acetate, propyl acetate, isopropyl acetate,
b) stirring the reaction mixture,
c) filtering the precipitated solid to get the crystalline form-N of 5-fluoro-3-phenyl-2-[(lS)-l-(9H-purin-6-ylamino)propyl]quinazolin-4(3H)-one compound of formula-1.
.The crystalline form-M of 5-fluoro-3-phenyl-2-[(IS)-l-(9H-purin-6-ylamino)propyl] quinazolin-4(3H)-one compound of formula-I obtained according to claims-1 and 3 is useful in the preparation of pharmaceutical composition.