新产品编号:563701
Chemical Name: 2-[8-(4-Chlorophenyl)-8-oxooctylsulfanyl]-5-(5-pyrimidinylmethyl)pyrimidin-4(1H)-one
CAS No. 224771-21-5
项目整合开发状态: Biological Testing
项目研究机构: GlaxoSmithKline (Originator)
合成路线:Palladium-catalyzed coupling of 5-bromopyrimidine (I) with ethyl acrylate (II) afforded pyrimidinyl acrylate (III),which was hydrogenated over Pd/C to give (IV).Claisen condensation of (IV) with ethyl formate furnished oxoester (V).This was then cyclized with thiourea (VI) to produce the intermediate thiouracil (VII).
合成路线:Friedel-Crafts acylation of chlorobenzene (VIII) with 8-bromooctanoyl chloride (IX) in the presence of AlCl3 gave rise to bromo ketone (X).Finally,alkylation of thiouracil (VII) with bromoketone (X) generated the title compound.
📌 参考资料/链接：
参考文献标题:Pyrimidinone cpds.and pharmaceutical compsns.containing them
文献作者:Pinto,I.L.; Ife,R.J.; Hickey,D.M.B.; Smith,S.A.; Leach,C.A.; Porter,R.A.(SmithKline Beecham plc)
参考来源:EP 1028955; WO 9924420
📄 详细内容
合成路线:Palladium-catalyzed coupling of 5-bromopyrimidine (I) with ethyl acrylate (II) afforded pyrimidinyl acrylate (III),which was hydrogenated over Pd/C to give (IV).Claisen condensation of (IV) with ethyl formate furnished oxoester (V).This was then cyclized with thiourea (VI) to produce the intermediate thiouracil (VII).
合成路线:Friedel-Crafts acylation of chlorobenzene (VIII) with 8-bromooctanoyl chloride (IX) in the presence of AlCl3 gave rise to bromo ketone (X).Finally,alkylation of thiouracil (VII) with bromoketone (X) generated the title compound.
参考文献标题:2-(Alkylthio)pyrimidin-4-ones as novel,reversible inhibitors of lipoprotein-associated phospholipase A2
文献作者:Boyd,H.F.; Flynn,S.T.; Hickey,D.M.; Ife,R.J.; Jones,M.; Leach,C.A.; Macphee,C.H.; Milliner,K.J.; Rawlings,D.A.; Slingsby,B.P.; Smith,S.A.; Stansfield,I.G.; Tew,D.G.; Theobald,C.J.
参考来源:Bioorg Med Chem Lett 2000,10(4),395