Thymine → HCID 54338636, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of thymine (5 g, 39.6 mmol), 1-fluoro-4-iodobenzene (9.68 g, 5 mL, 43.6 mmol), copper(I) oxide (6.24 g, 43.6 mmol) and 2,4,6-trimethylpyridine (200 mL) was heated 12 hours at reflux with stirring and under an argon atmosphere. The reaction mixture then was cooled to 25° C., diluted with methylene chloride (300 mL), washed with 5% sulfuric acid (5×300 mL) and concentrated. The residue was purified by flash chromatography on silica gel eluting with hexane/ethyl acetate (1:1) to give 1-(4-fluorophenyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (1.85 g, 9.2 mmol), m.p. 212°-214° C., and 3-(4-fluorophenyl)-5-methyl-2,4(1H,3H)-pyrimidinedione (2.39 g, 10.2 mmol), m.p. 229°-231° C.

Provenance & Evidence