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【结 构 式】

【分子编号】67993

【品名】1-(pentan-3-yl)-6-((trimethylsilyl)ethynyl)-1H-imidazo[4,5-b]pyrazin-2-ol

【CA登记号】 

【 分 子 式 】C15H22N4OSi

【 分 子 量 】302.452

【元素组成】C 59.57% H 7.33% N 18.52% O 5.29% Si 9.29%

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 2-amino-3,5-dibromopyrazine (I) with neat 3-amino-pentane (II) under microwave irradiation at 150 °C yields the diaminopyrazine (III), which is then subjected to cyclization with CDI in refluxing THF to give 6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol (IV). Sonogashira cross-coupling of aryl bromide (IV) with (trimethylsilyl)acetylene (V) in the presence of PdCl2(PPh3)2, CuI and Et3N in DMF at 80 °C affords adduct (VI), which is finally desilylated by treatment with KF in MeOH/THF/H2O .

1 Muci, A., Finer, J.T., Lu, P.-P., Russell, A.J., Morgan, B.P., Morgans, D.J. Jr. (Cytokinetics, Inc.). Certain chemical entities, compositions and methods. EP 2069352, JP 2009545596, US 2008146561, US 7598248, US 8227603, US 8299248, WO 200801669.
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) 26178 3,5-dibromo-2-pyrazinamine 24241-18-7 C4H3Br2N3 详情 详情
(II) 25924 1-ethylpropylamine; 3-pentanamine 616-24-0 C5H13N 详情 详情
(III) 67991 6-bromo-N2-(pentan-3-yl)pyrazine-2,3-diamine   C9H15BrN4 详情 详情
(IV) 67992 6-bromo-1-(3-pentyl)imidazo[4,5-b]pyrazin-2-ol   C10H13BrN4O 详情 详情
(V) 23897 ethynyl(trimethyl)silane;trimethylsilyl acetylene 1066-54-2 C5H10Si 详情 详情
(VI) 67993 1-(pentan-3-yl)-6-((trimethylsilyl)ethynyl)-1H-imidazo[4,5-b]pyrazin-2-ol   C15H22N4OSi 详情 详情
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