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【结 构 式】 
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【分子编号】28201 【品名】ethyl 4-[5-fluoro-4-(methylsulfanyl)-2-pyrimidinyl]-1-piperazinecarboxylate 【CA登记号】 |
【 分 子 式 】C12H17FN4O2S 【 分 子 量 】300.3571432 【元素组成】C 47.99% H 5.7% F 6.33% N 18.65% O 10.65% S 10.68% |
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：(III)The reaction of 2-chloro-5-fluoro-4-(methylsulfanyl)pyrimidine (I) with N-carbethoxypiperazine (II) yields (III), which upon treatment with Raney Nickel affords ethyl 4-(5-fluoro-2-pyrimidinyl)-1-piperazinecarboxylate (IV). Hydrolysis and decarboxylation of (IV) generates 5-fluoro-2-(1-piperazinyl)pyrimidine (V). The reaction of (V) with the alpha-chloroketal (VI) generates the butyrophenone derivative (VII). Sodium borohydride reduction of (VII) and treatment with ethanolic hydrochloric acid yields BMY-14802-1.
| 【1】 Lobeck, W.G. Jr.; Yevich, J.P. (Bristol-Myers Squibb Co.); Antipsychotic 1-fluorophenylbutyl-4-(2-pyrimidinyl)piperazine derivatives. AU 8539449; BE 0901880; CH 663022; DE 3507983; ES 8607254; FR 2560878; GB 2155925; JP 1986000075; US 4605655 . |
| 【2】 Yocca, F.D.; Yevich, J.P.; New, J.S.; BMY-14802-1. Drugs Fut 1987, 12, 8, 752. |
| 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) | 28200 | 2-chloro-5-fluoro-4-(methylsulfanyl)pyrimidine | C5H4ClFN2S | 详情 | 详情 | |
| (II) | 24694 | N-ethoxycarbonylpiperidine; Ethyl 1-piperazinecarboxylate; N-Ethoxycarbonyl piperazine; N-Carbethoxy piperazine | 120-43-4 | C7H14N2O2 | 详情 | 详情 |
| (III) | 28201 | ethyl 4-[5-fluoro-4-(methylsulfanyl)-2-pyrimidinyl]-1-piperazinecarboxylate | C12H17FN4O2S | 详情 | 详情 | |
| (IV) | 28202 | ethyl 4-(5-fluoro-2-pyrimidinyl)-1-piperazinecarboxylate | C11H15FN4O2 | 详情 | 详情 | |
| (V) | 11426 | 5-Fluoro-2-piperazinopyrimidine | C8H11FN4 | 详情 | 详情 | |
| (VI) | 28203 | 2-(3-chloropropyl)-2-(4-fluorophenyl)-1,3-dioxolane | 3308-94-9 | C12H14ClFO2 | 详情 | 详情 |
| (VII) | 28204 | 1-(4-fluorophenyl)-4-[4-(5-fluoro-2-pyrimidinyl)-1-piperazinyl]-1-butanone | C18H20F2N4O | 详情 | 详情 |
Extended Information