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Synthesis of 7‐aza‐5,8,10‐trideazafolic acid and its 4‐amino‐derivative as potential antifolates
Author(s) -
Wollein Günther,
Troschütz Reinhard
Publication year - 2002
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570390613
Subject(s) - chemistry , saponification , derivative (finance) , yield (engineering) , pyrimidine , guanidine , amide , medicinal chemistry , diamine , condensation , organic chemistry , stereochemistry , materials science , physics , financial economics , economics , metallurgy , thermodynamics
o ‐Aminoamide 8 , an intermediate in our multistep synthesisof the title compounds was prepared from 1,3‐diketone 3 . The following condensation of 8 with chloroformamidine‐HCl ( 9 ) gave pyrido[3,4‐ d ]pyrimidine 10 . Dehydratisation of amide 8 led to o ‐aminonitrile 15 , which was cyclocondensated with guanidine ( 16 ) to yield pyrido[3,4‐ d ]pyrimidine‐2,4‐diamine 17 . Coupling of the acids 11 and 18 with diethyl L‐glutamate ( 12 ) and following saponification provided 7‐aza‐5,8,10‐trideazafolic acid 14 and its 4‐amino‐derivative 20 .