Cyclopropanemethanamine → N-(Cyclopropylmethyl)-2-fluoro-9-isopropyl-9H-purine-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 cyclopropylmethylamine (0.24 g, 2.7 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 (290 mg, 83%) as a colorless gum. δH (CDCl3, 500 MHz) 0.29-0.27 (2 H, m, CHHCHH of Cp), 0.56-0.54 (2H, m, CHHCHH of Cp), 1.13 (1 H, s, br, CH of Cp), 1.58 (6 H, d, J 7.5, CH[CH3]2), 3.44 (2 H, s, br, NHCH2Cp) 2.97 (1 H, s, br, CH of Cp), 4.74-4.72 (1 H, m, CHMe2), 6.22 (1 H, s, br, NH), 7.76 (1 H, s, ArH); δC (CDCl3, 500 MHz) 160.09 (C), 156.14 (C), 147.4 (C), 137.38 (CH), 118.26 (C), 47.14 (CH), 45.78 (CH2), 22.46 (2×CH3), 10.06 (CH), 3.5 (2×CH2)

Provenance & Evidence