2-amino-4-methyl-3,5-pyridinedicarbonitrile -Drug Synthesis Database

【结构式】

【分子编号】35802

【品名】2-amino-4-methyl-3,5-pyridinedicarbonitrile

【CA登记号】

【分子式】C₈H₆N₄

【分子量】158.1626

【元素组成】C 60.75% H 3.82% N 35.42%

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：(V)

Condensation of malononitrile (I) with triethyl orthoacetate (II) in pyridine produced the intermediate (III), which was cyclized to pyridine (IV) by acidic treatment. Reductive dechlorination of (IV) by hydrogenation over Pd/BaCO3 afforded 2-aminopyridine-3,5-dicarbonitrile (V). Subsequent condensation of (V) with guanidine (VI) gave rise to the pyridopyrimidine system (VII). Finally, reductive amination of (VII) with 2-chloroaniline (VIII) by means of H2 and Raney-Ni afforded the title compound.

参考文献中间体

合成目标

【1】 Boutli, F.; Mourellou, O.; Avgoustinaki, N.; Zioga, M.; Rammnos, C.H.; Chin Journal of Medicinal Chemistry 1995, 5, 2, 79-85.
【2】 Gangjee, A.; Adair, O.; Queener, S.F.; Pneumocystis carinii Toxoplasma gondii dihydrofolate reductase inhibitors and antitumor agents: Synthesis and biological activities of 2,4-diamino-5-methyl-6-[(monosubstituted anilino)methyl]-pyrido[2,3-d]pyrimidines. J Med Chem 1999, 42, 13, 2447.

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)	12061	Malononitrile	109-77-3	C₃H₂N₂	详情	详情
(II)	12940	1,1-Diethoxyethyl ethyl ether; 1,1,1-Triethoxyethane; Triethyl orthoacetate	78-39-7	C₈H₁₈O₃	详情	详情
(III)	35800			C₁₃H₉N₅	详情	详情
(IV)	35801	2-amino-6-chloro-4-methyl-3,5-pyridinedicarbonitrile		C₈H₅ClN₄	详情	详情
(V)	35802	2-amino-4-methyl-3,5-pyridinedicarbonitrile		C₈H₆N₄	详情	详情
(VI)	14790	Guanidine	113-00-8	CH₅N₃	详情	详情
(VII)	35803	2,4-diamino-5-methylpyrido[2,3-d]pyrimidine-6-carbonitrile		C₉H₈N₆	详情	详情
(VIII)	35804	2-chloroaniline; 2-chlorophenylamine	95-51-2	C₆H₆ClN	详情	详情

Extended Information