6-chloro-3-nitro-2-pyridinecarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】29206

【品名】6-chloro-3-nitro-2-pyridinecarbonitrile

【CA登记号】

【分子式】C₆H₂ClN₃O₂

【分子量】183.5536

【元素组成】C 39.26% H 1.1% Cl 19.31% N 22.89% O 17.43%

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：(III)

2,6-Dichloropyridine (I) was nitrated with HNO3 and H2SO4 to give nitropyridine (II). Substitution of the 2-chloro atom of (II) with cuprous cyanide at 180 C afforded nitrile (III). The remaining 6-chloro atom of (III) was then substituted with N-methyl-3,4-dimethoxyaniline (IV) in monoethyl glycol in the presence of pyridine to provide diaryl amine (V). The nitro group of (V) was further reduced with iron powder and HCl yielding the 3-amino derivative (VI). Finally, cyclization of (VI) with chloroformamidine hydrochloride (VII) in dimethylsulfone at 140 C produced the target pyridopyrimidine.

参考文献中间体

合成目标

【1】 Gangjee, A.; Zhu, Y.; Queener, S.F.; 6-Substituted 2,4-diaminopyrido[3,2-d]pyrimidine analogues of piritrexim as inhibitors of dihydrofolate reductase from rat liver, Pneumocystis carinii, and Toxoplasma gondii and as antitumor agents. J Med Chem 1998, 41, 23, 4533.

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)	13573	2,6-Dichloropyridine	2402-78-0	C₅H₃Cl₂N	详情	详情
(II)	13574	2,6-Dichloro-3-nitropyridine	16013-85-7	C₅H₂Cl₂N₂O₂	详情	详情
(III)	29206	6-chloro-3-nitro-2-pyridinecarbonitrile		C₆H₂ClN₃O₂	详情	详情
(IV)	29207	3,4-dimethoxy-N-methylaniline		C₉H₁₃NO₂	详情	详情
(V)	29208	6-[3,4-dimethoxy(methyl)anilino]-3-nitro-2-pyridinecarbonitrile		C₁₅H₁₄N₄O₄	详情	详情
(VI)	29209	3-amino-6-[3,4-dimethoxy(methyl)anilino]-2-pyridinecarbonitrile		C₁₅H₁₆N₄O₂	详情	详情
(VII)	29210	chloroformamidine		CH₃ClN₂	详情	详情

Extended Information