Tin tetrachloride → HCID 57867413, compound

Participants

Reaction Steps

To a stirred solution of 6-chloro-9H-purin-2-amine (about 0.18 g, 1.08 mmol) in acetonitrile (about 6 ml) was added N,O-Bis(trimethylsilyl)acetamide (about 1.59 ml, 6.5 mmol) at room temperature and refluxed for about 2 hours. To this added (2R,4R)-5-(benzoyloxymethyl)-3-fluoro-3,4-dimethyltetrahydrofuran-2,4-diyl diacetate (about 0.20 g, 0.54 mmol) in acetonitrile (about 6 ml) drop wise at about 0° C., and added SnCl4 (about 0.09 ml, 0.81 mmol) then refluxed for about 2 hours. Completion of the reaction monitored by thin-layer chromatography and neutralized the reaction mixture with saturated sodium bicarbonate solution. Aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with water, brine and dried over sodium sulphate. Concentration under reduced pressure and purification by silica gel column chromatography using 2% methanol in dichloromethane as eluent furnished title compound (0.8 g) as a colorless solid. Yield: 33%; 1H NMR (300 MHz, CDCl3): δ 8.29 (d, 1H, J=4.2 Hz), 8.06-8.03 (m, 2H), 7.59-7.56 (m, 1H), 7.49-7.44 (m, 2H), 6.80 (d, 1H, J=21.6 Hz), 5.09 (s, 2H), 4.83-4.78 (m, 2H), 4.51-4.44 (m, 1H), 2.17 (s, 3H), 1.89 (d, 3H, J=2.4 Hz), 1.48 (d, 3H, J=23.1 Hz); ES Mass: [M+1] 478 (30%), [M+Na] 500 (30%); HPLC:. 93.1%.

Provenance & Evidence