Cyclobutylamine → N-Cyclobutyl-2-fluoro-9-isopropyl-9H-purin-6-amine

Participants

Reaction Steps

6-chloro-2-fluoro-9-isopropyl-9H-purine (0.3 g, 1.4 mmol), diisopropylethylamine (0.2 g, 1.55 mmol) and cyclobutylamine (0.2 g, 2.8 mmol) were stirred together in ethanol (30 ml) at room temperature for 6 h. Volatiles were removed and the residue taken up in ethyl acetate, washed with water (50 ml), brine (50 ml), dried (MgSO4) and concentrated. The crude was purified by silica gel flash column chromatography (ethyl acetate:hexane 3:2) to give the pure product (237 mg, 68%) δH (CDCl3, 500 MHz) 1.56 (6H, d, J 7.5, CH[CH3]2), 1.76-1.74 (2 H, m, CH2 of Cyclobutyl), 1.98-1.94 (2 H, m, CH2 of cyclobutyl), 2.45 (2 H, s, br, CH2 of cyclobutyl)) 4.72-4.7 (2 H, m, CH of cyclobutyl and CHMe2), 6.35 (1 H, s, br, NH), 7.75 (1 H, s, ArH); δC (CDCl3, 500 MHz) 160.08 (C), 158.43 (C), 155.34 (C), 155.18 (C), 150.09 (C), 137.44 (CH), 47.26 (CH), 31.56 (2×CH2), 22.38 (2×CH3), 15.09 (CH2); m/z 250.2 (M+H)

Provenance & Evidence