Allyl bromide → HCID 178460812, compound

Participants

Reaction Steps

This material was prepared by the procedure described in Tetrahedron 1985, 41, 5289-5293. To a solution of 5-fluoro-4-thioxo-3,4-dihydropyrimidin-2(1H)-one (12.4 g, 84.9 mmol) and sodium methoxide (4.54 g, 84.9 mmol) in MeOH (100 mL) was added dropwise allyl bromide (10.27 g, 84.9 mmol) at room temperature. The reaction mixture was stirred overnight at room temperature. After removal of solvent, the residue was purified by normal phase chromatography (gradient, 10 to 33% EtOAc/hexane), to give 4-(allylthio)-5-fluoropyrimidin-2(1H)-one (6 g, 38%) as a white solid: mp 150-152° C.; 1H NMR (301 MHz, DMSO-d6) δ 11.60 (s, 1H), 8.00 (d, J=4.5 Hz, 1H), 5.90 (ddt, J=16.8, 10.0, 6.8 Hz, 1H), 5.34 (dd, J=16.9, 1.4 Hz, 1H), 5.15 (dd, J=10.0, 0.7 Hz, 1H), 3.83 (d, J=6.8 Hz, 2H); ESIMS m/z 187 ([M+H]+).

Provenance & Evidence