Bropirimine
Chemical compound
From Wikipedia, the free encyclopedia
Bropirimine is an experimental drug with anti-cancer and antiviral properties.[citation needed] It is an orally effective immunomodulator and is being tried in bladder cancers.[1]
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| ECHA InfoCard | 100.231.001 |
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| Formula | C10H8BrN3O |
| Molar mass | 266.098 g·mol−1 |
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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 (because of the higher charge density). This tricarbonyl compound decarboxylates on acidification to the β-ketoester. Condensation with guanidine leads to the pyrimidone. NBS mediated bromination then gives bropirimine.
