Ammonia methanol → 2',3'-Dideoxy-3'-thiacytidine

Participants

Reaction Conditions

Reaction Steps

A solution of (2S*,5R*)-4-ethoxy-1-[2-(hydroxymethyl)-1,3-oxathiolan-5-yl]pyrimidin-2-one (0.21 g) in ammonia/methanol (8 mL of methanol saturated with ammonia gas at 0° C. for 45 minutes) was placed in a steel bomb with a teflon liner, sealed and heated at 70° C. for 18 hours. Solvent was evaporated in vacuo and the residue subjected to flash chromatography to give the desired product (0.16 g, 89%) as a white solid: mp 184-185° C.; 1H NMR (DMSO-d6): δ 3.00 (dd, J=11.8, 5.0 Hz, 1H), 3.38 (dd, J=11.8, 5.5 Hz, 1H), 3.63-3.80 (m, 2H), 5.15 (t, J=4.5 Hz, 1H), 5.30 (t, J=6.0 Hz, 1H), 5.70 (d, J=7.3 Hz, 1H); 6.18 (t, J=5.0 Hz, 1H), 7.20 (brd, 2H, NH2), 7.79 (d, J=7.3 Hz, 1H); MS m/z 229.8 (M+1, 4%), 112 (100%). Anal. Calcd. for C8H11N3O3S: C, 41.91; H, 4.84; N. 18.33; S, 13.99. Found: C, 41.97; H, 4.83; N, 18.24; S, 13.93

Provenance & Evidence