Methanol → HCID 68978433, compound

Participants

Reaction Steps

A solution of ((2R,4R)-3-acetoxy-5-(2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)-4-fluoro-3,4-dimethyl-tetrahydrofuran-2-yl)methyl benzoate (about 0.25 g, 0.59 mmol) in methanolic ammonia (25% w/w 10 ml) was stirred at room temperature for overnight. Completion of the reaction mixture monitored by thin-layer chromatography and methanol was removed under reduced pressure. Water added to the crude and extracted with ethyl acetate and the organic layer was dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 5% methanol in dichloromethane to elude title compound (0.09 g). Yield: 55%; 1H-NMR: 1H NMR (300 MHz, CDCl3): δ 8.57 (bs, 1H), 7.38-7.33 (m, 1H), 6.44 (d, 1H, J=22.2 Hz), 5.73 (d, 1H, J=8.1 Hz), 4.65 (bs, 1H), 4.19-4.09 (m, 3H), 2.86 (bs, 1H), 1.48 (s, 3H), 1.35 (d, 3H, J=2.6 Hz); ES Mass: [M+Na]+: 297 (20%), [M+1]+ 275 (20%); IR cm−: 3430 2928, 2864, 2273, 1707, 1385, 1270, 1052, 821, 567; HPLC: 93.2%.

Provenance & Evidence