Water → HCID 14182626, compound

Participants

Reaction Steps

4(3H)-Pyrimidone (0.772 g, 8 mmol) was dissolved in dimethylsulphoxide (10 ml) and treated with potassium tert-butoxide (0.440 g, 4 mmol). The mixture was stirred for 30 minutes at ambient temperature and 6-cyano-3,4-dihydro-2,2-dimethyl-3,4-epoxy-2H-1-benzopyran (1.278 g, 6 mmol) added. The resulting mixture was heated at 90° C. for 30 minutes, cooled and poured into water. Extractive work up with ethyl acetate yielded a gum which was purified by chromatography on silica (ethyl acetate) to give trans-6-cyano-3,4-dihydro-2,2-dimethyl-4-(6(1H)-pyrimidinon-1-yl)-2H-1-benzopyran-3-ol 0.703 g, (38%), mpt 202°-3° (ethyl acetate/hexane).

Provenance & Evidence