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【结 构 式】 
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【分子编号】25627 【品名】4-amino-6-chloro-2-pyrimidinylhydrosulfide 【CA登记号】 |
【 分 子 式 】C4H4ClN3S 【 分 子 量 】161.61468 【元素组成】C 29.73% H 2.49% Cl 21.94% N 26% S 19.84% |
合成路线1
该中间体在本合成路线中的序号：(VI)Alkylation of 4,6-dihydroxy-2-mercaptopyrimidine (I) with 4-methoxybenzyl chloride (II) provided methoxybenzyl sulfide (III). This was treated with POCl3 and 2-picoline to give dichloropyrimidine (IV). Then, ammonolysis with NH4OH in acetonitrile produced aminopyrimidine (V). Removal of the methoxybenzyl protecting group orf (V) was accomplished by treatment with methanesulfonic acid in CH2Cl2 to provide (VI). 4-Chlorocrotonyl chloride (VII) was condensed with diethylamine to yield chloro amide (VIII) (1). The title compound was then obtained by alkylation of mercaptopyrimidine (VI) with chloro amide (VIII) in the presence of NaOH in aqueous ethanol.
| 【1】 Murphy, M.J.; Schlachter, S.T.; Nugent, R.A.; et al.; Pyrimidine thioethers: A novel class of HIV-1 reverse transcriptase inhibitors with activity against BHAP-resistant HIV. J Med Chem 1998, 41, 20, 3793. |
| 【2】 Nugent, R.A.; et al. (Pharmacia & Upjohn AB); Alpha-substituted pyrimidine-thioalkyl and alkylester compounds as inhibitors of viral reverse transcriptase. EP 0824524; WO 9635678 . |
| 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) | 25623 | 2-Thiobarbituric acid; 4,5-Dihydroxy-2-mercaptopyrimidine; 2-sulfanyl-4,6-pyrimidinediol | 504-17-6 | C4H4N2O2S | 详情 | 详情 |
| (II) | 11910 | 4-Methoxybenzyl chloride; 1-(Chloromethyl)-4-methoxybenzene; alpha-Chloro-4-methoxytoluene; 4-(Chloromethyl)phenyl methyl ether | 824-94-2 | C8H9ClO | 详情 | 详情 |
| (III) | 25624 | 2-[(4-methoxybenzyl)sulfanyl]-4,6-pyrimidinediol | C12H12N2O3S | 详情 | 详情 | |
| (IV) | 25625 | 4,6-dichloro-2-[(4-methoxybenzyl)sulfanyl]pyrimidine | C12H10Cl2N2OS | 详情 | 详情 | |
| (V) | 25626 | 6-chloro-2-[(4-methoxybenzyl)sulfanyl]-4-pyrimidinamine | C12H12ClN3OS | 详情 | 详情 | |
| (VI) | 25627 | 4-amino-6-chloro-2-pyrimidinylhydrosulfide | C4H4ClN3S | 详情 | 详情 | |
| (VII) | 25629 | (E)-4-chloro-2-butenoyl chloride | C4H4Cl2O | 详情 | 详情 | |
| (VIII) | 25628 | (E)-4-chloro-N,N-diethyl-2-butenamide | C8H14ClNO | 详情 | 详情 |