ORG-41841
Chemical Name: 5-Amino-N-tert-butyl-4-(3-methoxyphenyl)-2-(methylsulfanyl)thieno[2,3-d]pyrimidine-6-carboxamide trifluoroacetate
CAS No. 301847-37-0 (free base)
项目整合开发状态: Preclinical
项目研究机构: Akzo Nobel (Originator)
合成路线:The condensation between 3-methoxybenzaldehyde (I),S-methylisothiourea (II) and ethyl cyanoacetate (III) in the presence of K2CO3 in hot EtOH leads to pyrimidine (IV).Subsequent chlorination of (IV) by means of POCl3 and dimethylaniline furnishes the 6-chloropyrimidine (V).Reaction of (V) with ethyl mercaptoacetate (VI) and potassium tert-butoxide gives rise to the thienopyrimidine (VII).The ethyl ester group of (VII) is then hydrolyzed to the carboxylic acid (VIII) employing LiOH.Finally,coupling of acid (VIII) with tert-butylamine by means of TBTU produces the target N-tert-butyl amide
📌 参考资料/链接：
参考文献标题:Bicyclic heteroaromatic cpds.useful as LH agonists
文献作者:Adang,A.E.P.; Gerritsma,G.G.; Van Straten,N.C.R.(Akzo Nobel N.V.)
参考来源:EP 1171443; JP 2002541259; US 6569863; WO 0061586
📄 详细内容
合成路线:The condensation between 3-methoxybenzaldehyde (I),S-methylisothiourea (II) and ethyl cyanoacetate (III) in the presence of K2CO3 in hot EtOH leads to pyrimidine (IV).Subsequent chlorination of (IV) by means of POCl3 and dimethylaniline furnishes the 6-chloropyrimidine (V).Reaction of (V) with ethyl mercaptoacetate (VI) and potassium tert-butoxide gives rise to the thienopyrimidine (VII).The ethyl ester group of (VII) is then hydrolyzed to the carboxylic acid (VIII) employing LiOH.Finally,coupling of acid (VIII) with tert-butylamine by means of TBTU produces the target N-tert-butyl amide
参考文献标题:Bicyclic heteroaromatic cpds.
文献作者:Timmers,C.M.; Karstens,W.F.J.(Akzo Nobel N.V.)
参考来源:WO 0224703
产品链接: CAS No. 301847-37-0››