新产品编号:2115643
Chemical Name: 6-(1-Naphthylsulfanylmethyl)pyrido[2,3-d]pyrimidine-2,4-diamine
项目整合开发状态: Biological Testing
项目研究机构: Duquesne University (Originator), Indiana University (Originator)
合成路线:Pyridine (III) was prepared by condensation of malononitrile (I) with triethyl orthoformate (II) in refluxing pyridine,followed by treatment with concentrated HCl.Dechlorination of (III) was effected by hydrogenolysis in the presence of Pd on BaCO3.The dechlorinated pyridine dinitrile (IV) was cyclized with guanidine (V),yielding the pyridopyrimidine (VI).Reduction of the nitrile function of (VI) to aldehyde (VII) was carried out using formic acid and Raney-Ni.This was further reduced to alcohol (VIII) with NaBH4.Bromination of the alcohol (VIII) by means of HBr resulted in bromide (IX).Nucleophilic displacement of the bromide group of (IX) with the sodium salt of 1-naphthalenethiol (X) afforded the target sulfide.
📌 参考资料/链接:
参考文献标题:Synthesis of 2,4-diamino-6-(thioarylmethyl)pyrido [2,3-d]pyrimidines as dihydrofolate reductase inhibitors
文献作者:Gangjee,A.; Adair,O.; Queener,S.F.
参考来源:Bioorg Med Chem 2001,9(11),2929