3-[6-(dimethylamino)-3-pyridinyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol -Drug Synthesis Database

【结构式】

【分子编号】53976

【品名】3-[6-(dimethylamino)-3-pyridinyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol

【CA登记号】n/a

【分子式】C₁₅H₁₇N₅O

【分子量】283.33308

【元素组成】C 63.59% H 6.05% N 24.72% O 5.65%

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：(VI)

The condensation of 2-[6-(dimethylamino)pyridin-3-yl]acetonitrile (I) with ethyl acetate (II) by means of NaH in THF gives 2-[6-(dimethylamino)pyridin-3-yl]-3-oxobutyronitrile (III), which is treated with hydrazine in refluxing ethanol/water to yield the corresponding hydrazone (IV). The cyclization of (IV) with ethyl acetoacetate (V) in refluxing dioxane affords 3-[6-(dimethylamino)pyridin-3-yl]-2,5-dimethylpyrazolo[2,3-a]pyrimidin-7-ol (VI), which is treated with refluxing POCl3 to provide the expected 7-chloro derivative (VII). Finally, this compound is treated with dipropylamine (VIII) in refluxing acetonitrile to furnish the target dipropylamino derivative.

参考文献中间体

合成目标

【1】 Chen, C.; Webb, T.R.; McCarthy, J.R.; Moran, T.J.; Wilcoxen, K.M. (Janssen Pharmaceutica NV; Neurocrine Biosciences Inc.); Pyrazolopyrimidines as CRF receptor antagonists. EP 0880523; JP 2000503661; WO 9729109 .

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)	53973	2-[6-(dimethylamino)-3-pyridinyl]acetonitrile	n/a	C₉H₁₁N₃	详情	详情
(II)	17491	ethyl acetate	141-78-6	C₄H₈O₂	详情	详情
(III)	53974	2-[6-(dimethylamino)-3-pyridinyl]-3-oxobutanenitrile	n/a	C₁₁H₁₃N₃O	详情	详情
(IV)	53975	2-[6-(dimethylamino)-3-pyridinyl]-3-[(Z)hydrazono]butanenitrile	n/a	C₁₁H₁₅N₅	详情	详情
(V)	11819	ethyl acetoacetate; ethyl 3-oxobutanoate；Acetoacetic ester;Ethyl beta-ketobutyrate;ethyl 3-oxobutyrate	141-97-9	C₆H₁₀O₃	详情	详情
(VI)	53976	3-[6-(dimethylamino)-3-pyridinyl]-2,5-dimethylpyrazolo[1,5-a]pyrimidin-7-ol	n/a	C₁₅H₁₇N₅O	详情	详情
(VII)	53977	N-[5-(7-chloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-2-pyridinyl]-N,N-dimethylamine; 5-(7-chloro-2,5-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)-N,N-dimethyl-2-pyridinamine	n/a	C₁₅H₁₆ClN₅	详情	详情
(VIII)	21856	N,N-dipropylamine; N-propyl-1-propanamine	142-84-7	C₆H₁₅N	详情	详情

Extended Information