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【结 构 式】

【分子编号】51672

【品名】6-chloro-2-fluoro-9H-purine

【CA登记号】

【 分 子 式 】C5H2ClFN4

【 分 子 量 】172.5489432

【元素组成】C 34.8% H 1.17% Cl 20.55% F 11.01% N 32.47%

与该中间体有关的原料药合成路线共 2 条

合成路线1

该中间体在本合成路线中的序号:(I)

The alkylation of 6-chloro-2-fluoropurine (I) with isopropanol (II) under Mitsunobu conditions gives 6-chloro-2-fluoro-9-isopropylpurine (III), which is regioselectively alkylated at the 6 position with 4-methoxybenzylamine (IV) to yield 2-fluoro-9-isopropyl-N6-(4-methoxybenzyl)adenine (V). Finally, the 2-fluoro position of (V) is aminated with perhydroazepine (VI) in n-butanol at high temperature in a sealed tube to afford the target trisubstituted purine.

1 Verdugo, D.E.; et al.; Discovery of estrogen sulfotransferase inhibitors from a purine library screen. J Med Chem 2001, 44, 17, 2683.
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) 51672 6-chloro-2-fluoro-9H-purine C5H2ClFN4 详情 详情
(II) 19250 2-propanol 67-63-0 C3H8O 详情 详情
(III) 51673 6-chloro-2-fluoro-9-isopropyl-9H-purine C8H8ClFN4 详情 详情
(IV) 15098 4-Methoxybenzylamine; (4-Methoxyphenyl)methanamine 2393-23-9 C8H11NO 详情 详情
(V) 51674 N-(2-fluoro-9-isopropyl-9H-purin-6-yl)-N-(4-methoxybenzyl)amine; 2-fluoro-9-isopropyl-N-(4-methoxybenzyl)-9H-purin-6-amine C16H18FN5O 详情 详情
(VI) 18672 azepane 111-49-9 C6H13N 详情 详情

合成路线2

该中间体在本合成路线中的序号:(II)

2-Amino-6-chloropurine (I) is converted into the 2-fluoro analogue (II) by diazotization in the presence of fluoroboric acid. Subsequent alkylation of (II) with EtOH under Mitsunobu conditions provides the 9-ethyl purine (III).

1 Weigele, M.; Sawyer, T.K.; Wang, Y.; Shakespeare, W.; Bohacek, R.; Sundaramoorthi, R.; Metcalf, C.A. III (Ariad Pharmaceuticals Inc.); Novel purines. WO 0144260 .
2 Weigele, M.; Sawyer, T.K.; Wang, Y.; Shakespeare, W.C.; Bohacek, R.; Sundaramoorthi, R.; Metcalf, C.A. III; Dalgarno, D.C. (Ariad Pharmaceuticals Inc.); Purine derivs.. WO 0144259 .
3 Weigele, M.; Sawyer, T.K.; Wang, Y.; Shakespeare, W.C.; Bohacek, R.; Sundaramoorthi, R.; Metcalf, C.A. III; Dalgarno, D.C. (Ariad Pharmaceuticals Inc.); Purine derivs.. US 2002068721 .
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) 11644 6-Chloro-9H-purin-2-amine; 6-Chloro-9H-purin-2-ylamine; 2-Amino-6-chloropurine 10310-21-1 C5H4ClN5 详情 详情
(II) 51672 6-chloro-2-fluoro-9H-purine C5H2ClFN4 详情 详情
(III) 61001 6-chloro-9-ethyl-2-fluoro-9H-purine C7H6ClFN4 详情 详情
Extended Information