Ammonia → Dideoxycytidine

Participants

Reaction Steps

A solution of 34 (0 6 g, 2.4 mmol ) in methanol saturated with ammonia (20 ml ) was stirred at 50° C. for 12 hours in a pressure vessel. The reaction mixture was concentrated and the residue was triturated with isopropanol, filtered, and dried to yield 0.4 g (80%) of 4: mp 207°-209° C. (benzene-ethanol); 1H NMR (DMSO-d6) δ 1.50-2.50 (4H, m, 2' and 3'-H), 3.63 (2H, m, 5'-H), 4.00 (1H, m, 4'-H), 4.96 (1H, t, J=4.9 Hz, OH), 5.69 (1H, d, J=7.25 Hz, 5-H), 5.95 (1H, m, 1'-H), 7.05 (2H, s, NH2), 7.89 (1 H, d, J=7.3 Hz, 6-H).

Provenance & Evidence