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Synthesis of 7-aza-5,8,10-trideazafolic acid and its 4-amino-derivative as potential antifolates

✍ Scribed by Günther Wollein; Reinhard Troschütz

Publisher: Journal of Heterocyclic Chemistry
Year: 2002
Tongue: English
Weight: 67 KB
Volume: 39
Category: Article
ISSN: 0022-152X
DOI: 10.1002/jhet.5570390613

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✦ Synopsis

Abstract

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.

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