Imidazole → HCID 178455235, compound

Participants

Reaction Steps

A mixture of inosine 13 (15.0 g, 56 mmol) (dried by coevaporation with 70 ml of dimethylformamide (DMF)), imidazole (9.52 g, 140 mmol) and tertbutyldimethylsilyl chloride (10.1 g, 67 mmol) in DMF (125 ml) was stirred at room temperature for 12 h. The solvent was removed in vacuo and the residue was purified chromatographically using CHCl3 -methanol (15:2) as the eluent to obtain 16.4 g (76.7%) of 18: mp softening at 220° C., melting at 229°-231° C. (CHCl3 -diethyl ether); 1H NMR (DMSO-d6) δ 0.0 (6H, s, (CH3)2Si), 0.82 (9H, s, (CH3)3CSi), 3.52-4.00 (3H, m, 4' and 5'-H), 4.10 (1H, t, J=4.8 Hz, 2'(3')-H), 4.41 (1H, t, J=4.8 HZ, 3'(2')-H), 5.83 (1H, d, J=5.3 HZ, 1'-H), 8.00 (1H, s, 8-H), 8.18 (1H, s, 2-H).

Provenance & Evidence