2',3'-Didehydro-2',3'-dideoxyuridine → 2',3'-Dideoxyuridine

Participants

Reaction Steps

A solution of 2',3'-dideoxy-2',3'-didehydrouridine (1.0 g, 4.8 mmol) in methanol (10 ml) containing a catalyst (wet 5% palladium on carbon) (400 mg) was stirred in an atmosphere of hydrogen for 1 h. The catalyst was removed by filtration and the filtrate was concentrated. The residue was chromatographed on silica gel (CHCl3 /MeOH=5/1) to give 2',3'-dideoxyuridine (0.99 g, 97% yield): Mp 121.2°-121.7° C.; εmax (MeOH) 262 nm (λ10560), εmin (MeOH) 232 nm (λ3810); 1H-NMR (Me2SO-d6)δ 1.74-2.00 (m, 3H), 2.20-2.35 (m, 1H), 3.49-3.55 (m, 1H), 3.64-3.69 (m, 1H), 4.00-4.03 (brs, 1H), 5.03 (s, 1H), 5.58 (d, 1H, J=8.06 Hz), 5.95 (m, 1H), 7.94 (d, 1H, J=8.06 Hz), 11.25 (brs, 1H); Fast atom bombardment mass spectrum m/z 213 (MH+). Anal. Calcd for C9H12N2O4 : C, 50.94; H, 5.70; N, 13.20. Found: C, 50.95; H, 5.71; N, 13.20.

Provenance & Evidence