Ammonia → Deoxycytidine

Participants

Reaction Steps

2′-deoxy-4-N-acetylcytidine is treated with methanolic ammonia overnight. The solution is concentrated in vacuo, and the residue is dissolved in water (100 mL) and is washed with dichloromethane (2×50 mL). The aqueous phase is evaporated in vacuo and the residue is purified on a column of Dowex 1-X2 (OH−)resin. The product is eluted with water, and the fractions are collected, evaporated and the residue is crystallized in methanol to give 2′-deoxycytidine (0.902 g, 84.6%). Melting point 208-210° C. 1H NMR (DMSO) d 1.94(dt, J=13.2, 6.1 Hz, 1, H2′), 2.12 (ddd, J=13.2, 6.0, 3.3 Hz, 1, H2″),3.07 (m, 2, H5′,5″), 3.77 (dd, J=6.9, 3.8 Hz, 1, H3′), 4.21 (dd, J=5.9, 3.2 Hz, 1, H4′), 5.02 (t, J=5.0 Hz, 1, OH5′), 5.23 (d, J=4.1 Hz, 1, OH3′), 5.75 (d, J=7.4 Hz, 1, H5), 6.17 (t, J=6.7 Hz, 1, H1′), 7.21 (br s, 2, NH2), 7.81 (d, J=7.4 Hz, 1, H6) ppm. MS (FAB) m/z 228.0990 (MH+[C9H14N3O4]=228.0984).

Provenance & Evidence