Improved synthesis process of diethyl N-[4-[(2,4-diaminopyrido[3,2-d] pyrimidin-6-yl) methylamino] benzoyl]-L-glutamate / 北京大学学报(医学版)
Journal of Peking University(Health Sciences)
; (6): 842-845, 2015.
Article
em Zh
| WPRIM
| ID: wpr-478001
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WPRO
ABSTRACT
Objective:
To establish a new approach to synthesis of diethyl N-[4-[(2,4-diaminopyrido [3,2-d]pyrimidin-6-yl)methylamino]benzoyl]-L-glutamate.Methods:
Target compound (5) was syn-thesized by the use of (2,4-dioxo-tetrahydropyridopyrimidin-6-yl) methyl acetate (1) as starting material via hydrolysis, chlorination, condensation with diethyl (p-aminobenzoyl)glutamate and aminolysis.Re-sultsA new approach to synthesis of diethyl N-[4-[(2,4-diaminopyrido[3,2-d]pyrimidin-6-yl)methyl-amino]benzoyl]-L-glutamatewas established .This synthetic route has hydrolysis reaction , chlorination, diethyl N-( p-aminobenzoyl )-L-glutamate condensation reaction and ammonolysis reaction .The total yield is 36.7%.The structures of those compounds have identified by 1 H nuclear magnetic resonance , 13 C nu-clear magnetic resonance and mass spectrometry .This synthetic route avoid the unstable brominated re-action product and improves the harsh condition of ammonolysis reaction .Conclusion:
The new synthetic route has improved the reaction condition and the stability of the intermediate , and increased the extent of the derivative compounds , which has great significance to anti-folic acid of anti-tumor inhibitor synthesis .
Texto completo:
1
Índice:
WPRIM
Idioma:
Zh
Revista:
Journal of Peking University(Health Sciences)
Ano de publicação:
2015
Tipo de documento:
Article