Imidazole → 5′-O-[(1,1-Dimethylethyl)dimethylsilyl]-5-methyluridine

Participants

Reaction Steps

A solution of 5-methyluridine (1.42 g, 5.49 mmol), imidazole (0,816 g, 11.26 mmol) and tertbutyldimethylsilyl chloride (0.9 g, 6.01 mmol) was stirred at room temperature for 24 hours and then concentrated in vacuo. The residue obtained was purified by chromatography on a silica gel column using CHCl3 -methanol (30:1) as the eluent to give 1.49 g (73%) of 5'-O-tert-butyldimethylsilyl-5-methyluridine as a colorless solid: mp 209°-211° C. (ethyl acetate); 1H NMR (DMSO-d6) δ 0.0 (6H, s, (CH3)2Si), 0.81 (9H, s, (CH3)3CSi), 3.60-3.90 (5H, m, 2, 3, 4' and 5'-H), 4.97 (1H, d, J=4.39 Hz, 3'-OH, exchangeable), 5.25 (1H, d, J=5.57 Hz, 2'-OH, exchangeable), 5.71 (1H, d, J=5.57 Hz, 1'-H), 7.32 (1H, s, 6-H), 11.21 (1H, s, NH, exchangeable).

Provenance & Evidence