MZPES
3-叠氮基乙胺嘧啶Chemical Name: 5-(3-Azido-4-chlorophenyl)-6-ethyl-2,4-pyrimidine-diamine monoethanesulfonate
CAS No. 95458-43-8, 95458-42-7 (diacetate), 95458-40-5 (free base), 95458-41-6 (monoHCl), 95458-44-9 (monomethanesulfonate)
项目整合开发状态: Phase II
项目研究机构: Aston University (Originator), GlaxoSmithKline (Originator)
合成路线:The nitration of 2,4-diamino-5-(4 chlorophenyl)-6-ethypyrimidine(pyrimethamine) (I) with HNO3 in H2SO4 gives 2,4-diamino-4-(4-chloro-3 nitrophenyl)- 6-ethylpyrimidine (II),which is reduced with SnCl2 in 10 N HCl or with hydrazine hydrate - Raney Nickel in 95% ethanol at 65 C to afford 2,4-diamino-5-(3-amino-4-chlorophenyl)-6-ethylpyrimidine (III).The diazotation of (III) with NaNO2 - HCl and treatment of the diazonium salt with sodium azide yields 2,4-diamino-5-(3-azido-4-chlorophenyl)-6-ethylpyrimidine (IV),which is treated finally with ethylsulfonic acid (V).
📌 参考资料/链接：
参考文献标题:Pyrimidine derivs.
文献作者:Bliss,E.A.; Griffin,R.J.; Stevens,M.F.G.(Aston University; Glaxo Wellcome plc)
参考来源:EP 0147443; GB 2152508; JP 1985502255; WO 8404746
📄 详细内容
合成路线:The nitration of 2,4-diamino-5-(4 chlorophenyl)-6-ethypyrimidine(pyrimethamine) (I) with HNO3 in H2SO4 gives 2,4-diamino-4-(4-chloro-3 nitrophenyl)- 6-ethylpyrimidine (II),which is reduced with SnCl2 in 10 N HCl or with hydrazine hydrate - Raney Nickel in 95% ethanol at 65 C to afford 2,4-diamino-5-(3-amino-4-chlorophenyl)-6-ethylpyrimidine (III).The diazotation of (III) with NaNO2 - HCl and treatment of the diazonium salt with sodium azide yields 2,4-diamino-5-(3-azido-4-chlorophenyl)-6-ethylpyrimidine (IV),which is treated finally with ethylsulfonic acid (V).
参考文献标题:Mzpes
文献作者:Castar,J.; Prous,J.
参考来源:Drugs Fut 1988,13(6),526
产品链接: CAS No.95458-40-5››