Ammonium Hydroxide → HCID 10446544, compound

Participants

Reaction Conditions

Reaction Steps

3',5'-Di-O-benzoyl-2'-O-methyl-5-trifluoromethyluridine (1.0 g, 2.1 mmoles) was dissolved in concentrated ammonium hydroxide (60 ml) and heated in a sealed tube at 55° C. for 16 hours. The solvent was removed under reduced pressure and the residue was chromatographed on silica gel (30 g) using a gradient of 0-5% methanol in CH2Cl2 to give 0.3 g (50% crude yield) of oil. A small portion of 2'-O-Methyl-5-cyanouridine crystallized from methanol as a slightly impure white solid, mp 208°-211° C. IR (potassium bromide pellet) 2240 cm-1 (sharp, CN); 1H NMR (DMSO-d6): δ3.45(s, 3H, OCH3), 3.5-3.6 (m, 1H, H-5'), 3.7-3.9 (m, 3H, H-3',4',5'), 4.13 (m, 1H, H-2'), 5.17 (d, J=6 Hz, 1H, 3'--OH), 5.48 (br t, 1H, 5'--OH), 5.75 (br s, 1H, H1'), 8.99 (d, J=1.5 Hz, 1H, H-6), 12.08 (br s, 1H, N--H). Anal. Calcd for C11H13N3O6 (283.24): C, 46.64; H, 4.63; N, 14.83. Found: C, 45.98; H, 4.63; N, 14.35.

Provenance & Evidence