4,6-dichloro-2-methylpyrimidine -Drug Synthesis Database

【结构式】

【分子编号】32323

【品名】4,6-dichloro-2-methylpyrimidine

【CA登记号】1780-26-3

【分子式】C₅H₄Cl₂N₂

【分子量】163.00564

【元素组成】C 36.84% H 2.47% Cl 43.5% N 17.19%

与该中间体有关的原料药合成路线共 4 条

合成路线1 合成路线2 合成路线3 合成路线4

合成路线1

该中间体在本合成路线中的序号：(I)

The condensation of 4,6-dichloro-2-methylpyrimidine (I) with 2,4,6-trichloroaniline (II) by means of NaH in THF gives N-(6-chloro-2-methylpyrimidin-4-yl)-N-(2,4,6-trichlorophenyl)amine (III), which is condensed with N-(cyclopropylmethyl)-N-propylamine (IV) by heating at 100-190 C yielding N-(cyclopropylmethyl)-N-[2-methyl-6-(2,4,6-trichlorophenylamino)-pyrimidin-4-yl]-N-propylamine (V). Finally, this compound is chlorinated with N-chlorosuccinimide (NCS) in refluxing chloroform.

参考文献中间体

合成目标

【1】 Dagnino, R. jr.; Chen, C.; de Souzza, E.B.; et al.; Design and synthesis of a series of non-peptide high-affinity human corticotropin-releasing factor1 receptor antagonists. J Med Chem 1996, 39, 22, 4360.

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)	32323	4,6-dichloro-2-methylpyrimidine	1780-26-3	C₅H₄Cl₂N₂	详情	详情
(II)	15466	2,4,6-Trichloroaniline; 2,4,6-Trichlorophenylamine	634-93-5	C₆H₄Cl₃N	详情	详情
(III)	32324	N-(6-chloro-2-methyl-4-pyrimidinyl)-N-(2,4,6-trichlorophenyl)amine; 6-chloro-2-methyl-N-(2,4,6-trichlorophenyl)-4-pyrimidinamine		C₁₁H₇Cl₄N₃	详情	详情
(IV)	27745	N-(cyclopropylmethyl)-1-propanamine	26389-60-6	C₇H₁₅N	详情	详情
(V)	32325	N-(cyclopropylmethyl)-N-[2-methyl-6-(2,4,6-trichloroanilino)-4-pyrimidinyl]-N-propylamine; N(4)-(cyclopropylmethyl)-2-methyl-N(4)-propyl-N(6)-(2,4,6-trichlorophenyl)-4,6-pyrimidinediamine		C₁₈H₂₁Cl₃N₄	详情	详情

合成路线2

该中间体在本合成路线中的序号：(I)

Condensation between 4,6-dichloro-2-methylpyrimidine (I) and 2,6-dichloro-4-iodoaniline (II) in the presence of NaH in THF furnished the diaryl amine (III). The remaining chlorine atom was displaced with N-(cyclopropylmethyl)propylamine (IV) in hot DMSO to yield (V). Finally, chlorination of the pyrimidine ring with N-chlorosuccinimide (NCS) afforded the target 4-iodo derivative.

参考文献中间体

合成目标

【1】 Hsin, L.-W.; Webster, E.L.; Tian, X.; et al.; The development of a potential single photon emission computed tomography (SPECT) imaging agent for the corticotropin-releasing hormone receptor type 1. Bioorg Med Chem Lett 2001, 11, 3, 331.

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)	32323	4,6-dichloro-2-methylpyrimidine	1780-26-3	C₅H₄Cl₂N₂	详情	详情
(II)	51390	2,6-dichloro-4-iodophenylamine; 2,6-dichloro-4-iodoaniline		C₆H₄Cl₂IN	详情	详情
(III)	51391	N-(6-chloro-2-methyl-4-pyrimidinyl)-N-(2,6-dichloro-4-iodophenyl)amine; 6-chloro-N-(2,6-dichloro-4-iodophenyl)-2-methyl-4-pyrimidinamine		C₁₁H₇Cl₃IN₃	详情	详情
(IV)	27745	N-(cyclopropylmethyl)-1-propanamine	26389-60-6	C₇H₁₅N	详情	详情
(V)	51392	N-(cyclopropylmethyl)-N-[6-(2,6-dichloro-4-iodoanilino)-2-methyl-4-pyrimidinyl]-N-propylamine; N(4)-(cyclopropylmethyl)-N(6)-(2,6-dichloro-4-iodophenyl)-2-methyl-N(4)-propyl-4,6-pyrimidinediamine		C₁₈H₂₁Cl₂IN₄	详情	详情

合成路线3

该中间体在本合成路线中的序号：（V)

参考文献中间体

合成目标

【1】 Chen B-C,DroghiniR,et aL 2006.Process for preparing 2-aminothiazole-5-carboxamides from thioureas and acrylamides and their use as anticancer drugs. US 2006004067

中间体序号	中间体编号	品名	CAS号	分子式	供应商	用于合成
（V)	32323	4,6-dichloro-2-methylpyrimidine	1780-26-3	C₅H₄Cl₂N₂	详情	详情
(I)	29789	2-chloro-6-methylphenylamine; 2-chloro-6-methylaniline	87-63-8	C₇H₈ClN	详情	详情
(II)	20616	(E)-3-ethoxy-2-propenoyl chloride	99471-66-6	C₅H₇ClO₂	详情	详情
(III)	66243	(E)-N-(2-chloro-6-methylphenyl)-3-ethoxyacrylamide	863127-76-8	C₁₂H₁₄ClNO₂	详情	详情
(IV)	66244	2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide	302964-24-5	C₁₁H₁₀ClN₃OS	详情	详情
(VI)	66245	2-((6-chloro-2-methylpyrimidin-4-yl)amino)-N-(2-chloro-6-methylphenyl)thiazolidine-5-carboxamide		C₁₆H₁₇Cl₂N₅OS	详情	详情
(VII)	21893	2-(1-piperazinyl)-1-ethanol; 1-piperazineethanol; 1-(2-Hydroxyethyl)piperazine	103-76-4	C₆H₁₄N₂O	详情	详情

合成路线4

该中间体在本合成路线中的序号：(I)

参考文献中间体

合成目标

【1】 Chen B-C, Droghini R, et al.2006. Process for preparing 2-aminothiazole-5-cadboxamides from thioureas and acrylamides and their use as anticancer drugs.US 2006004067

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)	32323	4,6-dichloro-2-methylpyrimidine	1780-26-3	C₅H₄Cl₂N₂	详情	详情
(II)	21893	2-(1-piperazinyl)-1-ethanol; 1-piperazineethanol; 1-(2-Hydroxyethyl)piperazine	103-76-4	C₆H₁₄N₂O	详情	详情
(III)	66253	2-(4-(6-chloro-2-methylpyrimidin-4-yl)piperazin-1-yl)ethanol;4-(6-chloro-2-methyl-4-pyrimidinyl)-1-Piperazineethanol	127116-19-2	C₁₁H₁₇ClN₄O	详情	详情
(IV)	66244	2-amino-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide	302964-24-5	C₁₁H₁₀ClN₃OS	详情	详情

Extended Information