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【结 构 式】

【分子编号】68680

【品名】N-(5-methyl-1H-pyrazol-3-yl)-6-(4-methylpiperazin-1-yl)-2-(phenylethynyl)pyrimidin-4-amine

【CA登记号】 

【 分 子 式 】C21H23N7

【 分 子 量 】373.461

【元素组成】C 67.54% H 6.21% N 26.25%

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)

Oxidation of 4,6-dichloro-2-(methylsulfanyl)pyrimidine (I) with 3-chlorobenzoyl peroxide in CH2Cl2 gives the sulfonyl derivative (II), which is alkynylated with phenylacetylenyl magnesium bromide (III) in THF to provide 4,6-dichloro-2-(phenylethynyl)pyrimidine (IV). Condensation of the dichloropyrimidine derivative (IV) with 5-methyl-3-aminopyrazole (V) by means of NaI and DIEA in DMA at 90 °C affords amine (VI), which is coupled with N-methylpiperazine (VII) in the presence of DMAP and DIEA in 1,4-dioxane at 100 °C to furnish the piperazinyl derivative (VIII). Reduction of alkyne (VIII) by means of LiAlH4 in THF gives alkene (IX), which is finally treated with sodium potassium tartrate .

1 Xiao, X.-Y., Patel, D.V., Ward, J.S., Bray, M.R., Agoston, G.E., Treston, A.M.(Miikana Therapeutics, Inc.). Substituted pyrazole compounds. EP 1928456, JP 2009510107, US 2007142368, WO 2007041358.
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) 65246 4,6-Dichloro-2-(methylthio)pyrimidine;4,6-dichloro-2-(methylsulfanyl)pyrimidine 6299-25-8 C5H4Cl2N2S 详情 详情
(II) 65247 4,6-Dichloro-2-(methylsulfonyl)pyrimidine; 2-(Methylsulfonyl)-4,6-Dichloropyrimidine; NSC 45040 4489-34-3 C5H4Cl2N2O2S 详情 详情
(III) 32758 bromo(2-phenylethynyl)magnesium;phenylacetylenyl magnesium bromide;(phenylethynyl)magnesium bromide C8H5BrMg 详情 详情
(IV) 68677 4,6-dichloro-2-(phenylethynyl)pyrimidine   C12H6Cl2N2 详情 详情
(V) 68679 5-methyl-3-aminopyrazole;3-Amino-5-methylpyrazole;3-Methyl-1H-pyrazol-5-amine 31230-17-8 C4H7N3 详情 详情
(VI) 68678 6-chloro-N-(5-methyl-1H-pyrazol-3-yl)-2-(phenylethynyl)pyrimidin-4-amine   C16H12ClN5 详情 详情
(VII) 10061 1-Methylpiperazine; 1-Methyl piperazine; N-Methylpiperazine 109-01-3 C5H12N2 详情 详情
(VIII) 68680 N-(5-methyl-1H-pyrazol-3-yl)-6-(4-methylpiperazin-1-yl)-2-(phenylethynyl)pyrimidin-4-amine   C21H23N7 详情 详情
(IX) 68681 N-(5-methyl-1H-pyrazol-3-yl)-6-(4-methylpiperazin-1-yl)-2-styrylpyrimidin-4-amine;6-(4-Methyl-1-piperazinyl)-N-(5-methyl-1H-pyrazol-3-yl)-2-[(1E)-2-phenylethenyl]-4-pyrimidinamine 934353-76-1 C21H25N7 详情 详情
Extended Information