【结 构 式】 |
【分子编号】38823 【品名】dicyclopropylmethanol 【CA登记号】14300-33-5 |
【 分 子 式 】C7H12O 【 分 子 量 】112.17168 【元素组成】C 74.95% H 10.78% O 14.26% |
合成路线1
该中间体在本合成路线中的序号:(VIII)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 |