Ammonium Hydroxide → Uridine, 2′,5′-dideoxy-2′-fluoro-

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Reaction Steps

2′,5′-Dideoxy-5′-iodo-2′-fluorouridine (2.9, 8.1 mmoles) was dissolved in 95% ethanol (25 mL). Ammonium hydroxide (1.1 mL, 16.2 mmoles, 2 eq.) was added followed by 10% Pd/C (Aldrich, 0.1 g). Reaction under 50 psi hydrogen was carried out for 5 hours. The mixture was filtered and the pH adjusted to 7 with 1N HCl. The solvents were removed in vacuo and the residue dissolved in water. The product was extracted with ethyl acetate (3×). The ethyl acetate solution was dried with MgSO4, filtered, and the solvent removed in vacuo. The residue was purified by chromatography on 100 g of silica gel eluted with ethyl acetate. The product containing fractions were combined and the solvents removed in vacuo. The yield was 1.1 g, 58%. MS (APCl(−)): m/z (rel. intensity) 229 (100%, M−); 1H NMR (DMSO-d6) δ7.54 (d, 1H, H6, J=8 Hz), 5.76 (d, 1H, H-1′, J=22 Hz), 5.59 (d,1H, H5, J=8 Hz), 5.55 (d, 1H, OH, J=6 Hz), 5.05 (d, 1H, H-2′, J=53 Hz), 3.8 (m, 2H), 1.27 (d, 3H, H-5′, J=6 Hz).

Provenance & Evidence