2-Bromopropane → 2-Fluoro-9-isopropyl-N-((3-methylpyridin-2-yl)methyl)-9H-purin-6-amine

Participants

Reaction Steps

To a stirred solution of 2-fluoro-N-(3-methylpyridin-2-yl)methyl-9H-purin-6-amine (0.3 g, 1.17 mmol) in dimethylformamide (10 ml) at room temperature under an argon atmosphere, was added powdered, anhydrous K2CO3 (0.8 g, 5 eq, 5.85 mmol), followed by 2-bromopropane (1.15 ml, 11.7 mmol). The reaction mixture was stirred at room temperature for 24 h, when DCM:ether:MeOH (55:40:5), indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between EtOAc (50 ml) and water (50 ml). The aqueous phase was extracted with more EtOAc (2×50 ml) and the combined organic phase washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo. The residue was purified by silica gel column chromatography, eluted with CHCl3:MeOH (98:2) to afford the title compound as a slightly yellow film (170 mg, 48%). δH (CDCl3, 500 MHz) 1.51 (6 H, d, J 7.5, CH[CH3]2), 2.28 (3 H, s, CH3), 4.68-4.65 (3H, m, NHCH2 and CHMe2), 7.08-7.05 (1 H, m, ArH), 7.4 (1 H, d, J 5, ArH), 7.72 (1 H, s, ArH), 7.93 (1H, s, br, NH), 8.34 (1 H, d, J 5, ArH); δC (CDCl3, 500 MHz) 160.09 (C), 158.43 (C), 155.97 (C), 154.06 (C), 145.85 (CH), 137.73 (CH), 137.54 (CH), 130.67 (C), 122.28 (CH), 118.73 (C), 47.28 (CH), 42.87 (CH2), 22.43 (2×CH3), 17.66 (CH3); 19F NMR δ −50.20; m/z 301.2 (M+H)

Provenance & Evidence