Journal of Heterocyclic Chemistry p. 703 - 706 (1999)
Update date:2022-08-04
Topics:
Troschuetz, Reinhard
Zink, Mario
Gnibl, Rainer
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 3E/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 3E/Z, with 2,4,6-triaminopyrimidine (4) yielded iso-piritrexim (5).
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(1953)
