Methanol → HCID 44230605, compound

Participants

Reaction Steps

A solution of ((2R,4R)-3-acetoxy-5-(6-(cyclopentylamino)-9H-purin-9-yl)-4-fluoro-3,4-dimethyltetrahydrofuran-2-yl)methyl benzoate (about 0.31 g, 0.60 mmol) in methanolic ammonia (25% w/w 15 ml) was stirred at room temperature for overnight. Completion of the reaction monitored by thin-layer chromatography and methanol was removed under reduced pressure then water added to the crude and extracted with ethyl acetate. The organic layer was dried over sodium sulphate, concentrated under reduced pressure and purified by silica gel column chromatography using 5% methanol in dichloromethane to afford the title compound (0.2 g) as a colorless solid. Yield: 90%; 1H NMR (300 MHz, CDCl3): δ 8.33 (s, 1H), 7.92 (d, 1H, J=3.6 Hz), 6.62 (d, 1H, J=22.2 Hz), 5.83 (bs, 1H), 5.55 (s, 1H), 5.43 (bs, 1H), 4.58 (bs, 1H), 4.25-4.21 (m, 2H), 4.14-4.10 (m, 1H), 2.15-2.09 (m, 1H), 1.78-1.52 (m, 8H), 1.42-1.25 (m, 6H); ES Mass: [M+1]+ 366 (100%), 367 (45%); IR cm−: 3306, 2959, 1624, 1475, 1232, 1056, 938, 812; HPLC: 98.2%.

Provenance & Evidence