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

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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.; λmax(MeOH) 262 nm (ε 10560), λmin(MeOH) 232 nm (ε 3810); 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.

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