Bropirimine


Bropirimine is an experimental drug with anti-cancer and antiviral properties. It is an orally effective immunomodulator and is being tried in bladder cancers.

Synthesis

For the first step, the dianion from malonic acid half-ester is formed by treatment with butyllithium. Acylation of the anion with benzoyl chloride proceeds at the carbanion, which is more nucleophilic. This tricarbonyl compound decarboxylates on acidification to the β-ketoester. Condensation with guanidine leads to the pyrimidone. NBS mediated bromination then gives bropirimine.