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An alternative synthesis of piritrexim, a lipophilic inhibitor of human dihydrofolate-reductase

✍ Scribed by Reinhard Troschütz; Mario Zink; Rainer Gnibl

Publisher
Journal of Heterocyclic Chemistry
Year
1999
Tongue
English
Weight
308 KB
Volume
36
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

An alternative synthesis of the lipophilic antifolate piritrexim (1) is outlined. Starting from ketone 2, treatment with phosphorus oxychloride and dimethylformamide gave the β‐chlorocrotonaldehydes 3__E/Z__, which were reacted with cyanoacetamide (6) in the presence of sodium hydride to yield a 3‐cyano‐2‐pyridone derivative 7. Chlorination of 7 with thionyl chloride and subsequent reaction with guanidine (9) gave rise to piritrexim (1). The reaction of β‐chlorocrotonaldehydes 3__E/Z__, with 2,4,6‐triaminopyrimidine (4) yielded iso‐piritrexim (5).

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