Tetrabutylammonium Fluoride → 9-[(2R,5S)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]-3H-purin-6-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 21 (3.0 g, 8.6 mmol) in dry tetrahydrofuran (THF) (65 ml), cooled in an ice-bath, was added a 1M solution of tetra-n-butylammonium fluoride in THF (34 ml, 34.0 mmol). The mixture was stirred at 0° C. for 30 minutes, and the solvent was evaporated under vacuum. The residue was purified by chromatography on a silica gel column using CHCl3 methanol (7:1) as the eluent. Concentration of the TLC purified fractions yielded 1.36 g (67%) of 8: mp >310° C. (methanol); 1H NMR (DMSO-d6) δ 3.56 (2H, d, J =2.6 Hz, 5'-H), 4.84 (2H, m, 4'-H and OH, collapses to a multiplet integrating to one proton after D20 exchange), 6.12 (1H, br d, J=5.7 Hz, 2'-H), 6.47 (1 H, br d, J=5.7 Hz, 3'-H), 6.90 (1H, m, 1'-H), 8.06 (1H, s, 8-H), 8.10 (1H, s, 2-H), 12.40 (1H, br s, NH).

Provenance & Evidence