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【结 构 式】

【分子编号】54378

【品名】2-chloro-N-mesityl-4-pyrimidinamine; N-(2-chloro-4-pyrimidinyl)-N-mesitylamine

【CA登记号】

【 分 子 式 】C13H14ClN3

【 分 子 量 】247.72708

【元素组成】C 63.03% H 5.7% Cl 14.31% N 16.96%

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:(VIII)

The synthesis can be performed by two related ways: 1) The condensation of 2-(methylsulfanyl)pyrimidin-4-ol (I) with 4-aminobenzonitrile (II) in hot diglyme gives 4-(4-hydroxypyrimidin-2-ylamino)benzonitrile (III), which is treated with POCl3 to yield the corresponding chloro derivative (IV). Finally, this compound is condensed with 2,4,6-trimethylaniline (V) in dioxane to afford the target 4-aminobenzonitrile derivative. 2) Condensation of 2,4,6-trimethylaniline (VI) with 2,4-dichloropyrimidine (VII) by means of DIEA in refluxing 1,4-dioxane, followed by chromatographic purification furnishes intermediate (VIII), which is finally converted into the desired compound by condensation with 4-aminobenzonitrile (II) in refluxing water by means of HCl in 2-propanol.

2 Heeres, J.; Kukla, M.J.; Andries, K.J.L.M.; Janssen, P.A.J.; Ho, C.Y.; Janssen, M.A.C.; Ludovici, D.W.; de Corte, B.; de Jonge, M.R.; Koymans, L.M.H.; van Aken, K.J.A. (Janssen Pharmaceutica NV); HIV inhibiting pyrimidine derivs.. EP 0945442; EP 0945443; US 6197779; US 6440986; WO 9950250 .
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) 54374 2-Methylsulfanylpyrimidin-4-ol; 2-Methylthio-4-hydroxy pyrimidine 124700-70-5 C5H6N2OS 详情 详情
(II) 15361 4-Aminobenzonitrile 873-74-5 C7H6N2 详情 详情
(III) 54375 4-[(4-hydroxy-2-pyrimidinyl)amino]benzonitrile; 4-[(1,4-Dihydro-4-oxo-2-pyrimidinyl)amino]benzonitrile 189956-45-4 C11H8N4O 详情 详情
(IV) 54376 4-[(4-chloro-2-pyrimidinyl)amino]benzonitrile 244768-32-9 C11H7ClN4 详情 详情
(V) 28804 2,4,6-trimethylaniline 88-05-1 C9H13N 详情 详情
(VII) 54377 2,4-Dichloropyrimidine 3934-20-1 C4H2Cl2N2 详情 详情
(VIII) 54378 2-chloro-N-mesityl-4-pyrimidinamine; N-(2-chloro-4-pyrimidinyl)-N-mesitylamine C13H14ClN3 详情 详情
Extended Information