Isopropyl iodide → 6-Chloro-2-fluoro-9-isopropyl-9H-purine

Participants

Reaction Steps

A mixture of 2-fluoro,6-chloro-purine (2 g, 11.7 mmol), and powdered potassium carbonate (4 g, 28 mmol) was vigorously stirred in 30 ml DMF. Isopropyliodide (6 ml, 60 mmol) was added very slowly over 2 h. The reaction was stirred for a further 5 h. DMF was removed and the crude taken up in ethyl acetate, washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated. The crude was purified by silica gel column chromatography (30% ethyl acetate in hexane) to provide the pure product as a white solid (1.1 g, 44%). δH (CD3OD, 250 MHz) 1.65 [6 H, d, J 7.5, CH(CH3)2], 4.92 [1 H, m, CH(CH3)2], 8.66 (1 H, s, ArH); δC (CD3OD, 250 MHz) 154.7 (C), 153.88 (C), 152.2 (C), 147.65 (CH), 132.44 (C), 50.66 (CH), 22.72 (2×CH3); m/z 215.2 (M+H)

Provenance & Evidence