Ammonia → 2',3'-Didehydro-2',3'-dideoxyguanosine

Participants

Reaction Steps

A solution of 27 (0.3 g, 0.94 mmol) in methanol saturated with ammonia (20 ml) was stirred at 50°-55° C. for 12 hours in a pressure vessel. The reaction mixture was cooled to room temperature. The solid obtained was filtered, washed with cold isopropanol, and dried. Crystallization from methanol afforded 0.2 g (81%) of 9 as an amorphous solid: mp >250° C.; UV (methanol) λmax (pH 1) 270 mn, 251; (pH 7) 269 (sh), 255; (pH 11) 268; 1H NMR (DMSO-d6) 63.48-3.59 (2H, m, 5'-H), 4.70-5.00 (2H, m, 4'-H and OH), 6.08 (1H, br d, J=5.93 Hz, 2'-H), 6.40-6.47 (3H, m, 3'-H and NH2), 6.68 (1H, m, 1'-H), 7.70 (1H, s, 8-H).

Provenance & Evidence