5,6-Dihydropyrrolo[1,2-c]pyrimidine-1,3(2H,5H)-diones as annulated analogues of the anti-HIV compound MKC-442 (6-benzyl-1-(ethoxymethyl)-5-isopropyluracil)

Article abstract of DOI:10.1055/s-1997-1298

Annulated analogues of the anti-HIV compound MKC-442 were synthesized from 6-benzoyl-5-ethyl-2,4-dimethoxypyrimidine (4) by reaction with Zn/NH₄Cl and 3-bromopropene. The intermediate homoallylic alcohol is subjected to a ring closure reaction by treatment with bromine either directly or after O-benzylation to give 5,6-dihydropyrrolo[1,2-c]pyrimidinones. No activity against HIV was observed, neither for the annulated analogues nor the derivatives synthesized from 4. Only compound 4 showed activity against HIV-1.