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【结 构 式】

【分子编号】47053

【品名】triethyl 3-[2-chloro-6-(methylamino)-9H-purin-9-yl]-1,1,1-propanetricarboxylate

【CA登记号】

【 分 子 式 】C18H24ClN5O6

【 分 子 量 】441.87136

【元素组成】C 48.93% H 5.47% Cl 8.02% N 15.85% O 21.72%

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:(V)

The sodium salt of triethyl methanetricarboxylate (I) was alkylated with 1,2-dibromoethane (II) to afford bromide (III). Subsequent condensation of 6-(methylamino)-2-chloropurine (IV) with bromide (III) in the presence of K2CO3 gave adduct (V). Mono-decarbethoxylation of tricarboxylate (V) upon treatment with NaOMe produced malonate (VI), which was further reduced to diol (VII) by means of NaBH4 in CH2Cl2-MeOH. Treatment of (VII) with tetrabenzyl pyrophosphate in the presence of LDA gave rise to the bis-phosphate ester (VIII). The benzyl groups of (VIII) were then cleaved employing boron trichloride, and the resulting phosphoric acid was purified through an ion-exchange resin in the presence of ammonium bicarbonate to furnish the title tetraammonium salt.

1 Boyer, J.L.; Nandanan, E.; Kim, Y.-C.; Adams, M.; Harden, T.K.; Jang, S.-Y.; Jacobson, K.A.; Gallo-Rodriguez, C.; Acyclic analogues of deoxyadenosine 3',5'-bisphosphates as P2Y1 receptor antagonists. J Med Chem 2000, 43, 4, 746.
中间体序号 中间体编号 品名 CAS号 分子式 供应商 用于合成
(I) 47051 triethyl methanetricarboxylate 6279-86-3 C10H16O6 详情 详情
(II) 10252 1,2-Dibromoethane; Ethylene dibromide 106-93-4 C2H4Br2 详情 详情
(III) 11646 triethyl 3-bromo-1,1,1-propanetricarboxylate C12H19BrO6 详情 详情
(IV) 47052 2-chloro-N-methyl-9H-purin-6-amine; N-(2-chloro-9H-purin-6-yl)-N-methylamine C6H6ClN5 详情 详情
(V) 47053 triethyl 3-[2-chloro-6-(methylamino)-9H-purin-9-yl]-1,1,1-propanetricarboxylate C18H24ClN5O6 详情 详情
(VI) 47054 diethyl 2-[2-[2-chloro-6-(methylamino)-9H-purin-9-yl]ethyl]malonate C15H20ClN5O4 详情 详情
(VII) 47055 2-[2-[2-chloro-6-(methylamino)-9H-purin-9-yl]ethyl]-1,3-propanediol C11H16ClN5O2 详情 详情
(VIII) 47056 dibenzyl 2-([[bis(benzyloxy)phosphoryl]oxy]methyl)-4-[2-chloro-6-(methylamino)-9H-purin-9-yl]butyl phosphate C39H42ClN5O8P2 详情 详情
Extended Information