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【结 构 式】

【分子编号】48924

【品名】Methyl 3-amino-6-bromo-2-pyrazinecarboxylate

【CA登记号】

【 分 子 式 】C6H6BrN3O2

【 分 子 量 】232.03666

【元素组成】C 31.06% H 2.61% Br 34.44% N 18.11% O 13.79%

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:(I)

Treatment of methyl 6-bromo-3-amino-2-pyrazinecarboxylate (I) with sodium nitrite (NaNO2) in H2SO4 followed by refluxing in MeOH yields methoxy derivative (II), whose Br group is converted into an amino functionality by treatment with benzophenone-imine, tris(dibenzylidene-acetone)dipalladium, (S)-(-)-2,2'-bis(diphenylphosphino)-1,1'-binaphthyl and sodium tert-butoxide in toluene; a final treatment with HCl in THF affords amino compound (III). Treatment of methyl carboxylate of (III) with NH3(g) in MeOH gives carboxamide (IV), which is then treated with pyridine hydrofluoride and NaNO2 to furnish fluoro derivative (V). Finally, the target product is obtained by conversion of the methoxy group of (V) into a hydroxy group by reaction with NaI and trimethylsilyl chloride (TMSCl) in acetonitrile.

1 Furuta, Y.; Egawa, H. (Toyama Chemical Co., Ltd.); Nitrogenous heterocyclic carboxamide derivs. or salts thereof and antiviral agents containing both. EP 1112743; WO 0010569 .
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) 48924 Methyl 3-amino-6-bromo-2-pyrazinecarboxylate C6H6BrN3O2 详情 详情
(II) 48925 methyl 6-bromo-3-methoxy-2-pyrazinecarboxylate C7H7BrN2O3 详情 详情
(III) 32024 diphenylmethanimine 1013-88-3 C13H11N 详情 详情
(IV) 48926 methyl 6-amino-3-methoxy-2-pyrazinecarboxylate C7H9N3O3 详情 详情
(V) 48927 6-amino-3-methoxy-2-pyrazinecarboxamide C6H8N4O2 详情 详情
(VI) 48928 6-fluoro-3-methoxy-2-pyrazinecarboxamide C6H6FN3O2 详情 详情
Extended Information