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【结 构 式】 
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【分子编号】55737 【品名】4-[(4,6-dichloro-2-pyrimidinyl)amino]benzonitrile 【CA登记号】 |
【 分 子 式 】C11H6Cl2N4 【 分 子 量 】265.101 【元素组成】C 49.84% H 2.28% Cl 26.75% N 21.13% |
合成路线1
该中间体在本合成路线中的序号：(IV)The cyclization of 4-guanidinobenzonitrile (I) with diethyl malonate (II) by means of NaOEt in ethanol gives 4-(4,6-dihydroxypyrimidin-2-ylamino)benzonitrile (III), which is treated with POCl3 to yield the corresponding dichloro derivative (IV). The bromination of (IV) with Br2 and NaHCO3 in methanol/water affords 4-(5-bromo-4,6-dichloropyrimidin-2-ylamino)benzonitrile (V), which is condensed with sodium 4-cyano-2,6-dimethylphenolate (VI) and N-methylpyrrolidone in dioxane to provide the chloro precursor (VII). Finally, this compound is treated with ammonia in isopropanol to yield the target dinitrile derivative.
| 【1】 Ludovici, D.W.; De Corte, B.L.; Kukla, M.J.; et al.; Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues. Bioorg Med Chem Lett 2001, 11, 17, 2235. |
| 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) | 55735 | N-(4-cyanophenyl)guanidine | C8H8N4 | 详情 | 详情 | |
| (II) | 16829 | Diethyl malonate | 105-53-3 | C7H12O4 | 详情 | 详情 |
| (III) | 55736 | 4-[(4,6-dihydroxy-2-pyrimidinyl)amino]benzonitrile | C11H8N4O2 | 详情 | 详情 | |
| (IV) | 55737 | 4-[(4,6-dichloro-2-pyrimidinyl)amino]benzonitrile | C11H6Cl2N4 | 详情 | 详情 | |
| (V) | 46617 | 4-[(5-bromo-4,6-dichloro-2-pyrimidinyl)amino]benzonitrile | C11H5BrCl2N4 | 详情 | 详情 | |
| (VI) | 55738 | sodium 4-cyano-2,6-dimethylbenzenolate | C9H8NNaO | 详情 | 详情 | |
| (VII) | 55739 | ethyl 1-(2-{[(1S)-1-phenylethyl]amino}acetyl)cyclopropanecarboxylate | C16H21NO3 | 详情 | 详情 |