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【结 构 式】

【分子编号】38821

【品名】9-benzyl-6-[2-chloro-4-(trifluoromethyl)phenyl]-8-ethyl-9H-purine

【CA登记号】

【 分 子 式 】C21H16ClF3N4

【 分 子 量 】416.8329096

【元素组成】C 60.51% H 3.87% Cl 8.51% F 13.67% N 13.44%

与该中间体有关的原料药合成路线共 1 条

合成路线1

该中间体在本合成路线中的序号:(VI)

Condensation of 5-amino-4,6-dichloropyrimidine (I) with benzylamine afforded diamine (III). Subsequent reaction of (III) with triethyl orthopropionate in the presence of HCl produced imidate (IV), which was cyclized to purine (V) upon heating in diphenyl ether in the presence of p-toluenesulfonic acid. Palladium catalyzed coupling of (IV) with the organozinc derivative generated from Grignard reagent (V) and ZnCl2 produced the corresponding 6-aryl purine (VI). The N-benzyl group of (VI) was then deprotected by hydrogenation in the presence of palladium catalyst and trifluoroacetic acid to furnish (VII). Finally, condensation with dicyclopropylcarbinol (VIII) under Mitsunobu conditions yielded the title compound.

1 Beck, J.P.; Arvanitis, A.G.; Bakthavatchalam, R.; Wilde, R.G. (DuPont Pharmaceuticals Co.); Imidazopyrimidines and imidazopyridines for the treatment of neurological disorders. EP 0994877; WO 9901454 .
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
15147 Benzylamine; Phenylmethanamine 100-46-9 C7H9N 详情 详情
(I) 22845 5-Amino-4,6-dichloropyrimidine; 4,6-dichloro-5-pyrimidinylamine; 4,6-dichloro-5-pyrimidinamine 5413-85-4 C4H3Cl2N3 详情 详情
(II) 38817 N(4)-benzyl-6-chloro-4,5-pyrimidinediamine; N-(5-amino-6-chloro-4-pyrimidinyl)-N-benzylamine C11H11ClN4 详情 详情
(III) 38818 ethyl N-[4-(benzylamino)-6-chloro-5-pyrimidinyl]propanimidoate C16H19ClN4O 详情 详情
(IV) 38819 9-benzyl-6-chloro-8-ethyl-9H-purine C14H13ClN4 详情 详情
(V) 38820 bromo[2-chloro-4-(trifluoromethyl)phenyl]magnesium C7H3BrClF3Mg 详情 详情
(VI) 38821 9-benzyl-6-[2-chloro-4-(trifluoromethyl)phenyl]-8-ethyl-9H-purine C21H16ClF3N4 详情 详情
(VII) 38822 6-[2-chloro-4-(trifluoromethyl)phenyl]-8-ethyl-9H-purine C14H10ClF3N4 详情 详情
(VIII) 38823 dicyclopropylmethanol 14300-33-5 C7H12O 详情 详情
Extended Information