Reaction Steps
To a stirred solution of 2-fluoro-6-[(pyridin-3-ylmethyl)-amino]purine (1 g, 4.10 mmol) in DMF (12 ml) under argon atmosphere, at RT, was added K2CO3 (powdered, anhydrous, 2.84 g, 5 eq, 20.52 mmol) followed by (bromomethyl)cyclopropane (5.53 g 10 eq, 41 mmol). The reaction mixture was stirred at RT for 24 h, when TLC (CHC13: Me0H; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue partitioned between water (50 ml) and EtOAc (50 mL); the aqueous phase was separated and extracted with more EtOAc (2×50 ml). The bulked organic phase was washed with brine (50 ml), dried (MgSO4) and evaporated in vacuo, and the residue was purified by gradient flash column chormoatography on silica gel, eluted with CHCl3:MeOH (100:0→95:5), to afford the product as a colorless gum; Yield 0.8 g (68%) δH (250 MHz, CDCl3) 0.24-0.15 (2 H, m, CHH and CHH of Cp), 0.48-0.38 (2 H, m, CHH and CHH of Cp), 1.11-0.95 (1 H, m, CH of Cp), 2.56 (1 H, s, br, NH), 3.69 (2 H, d, J 7.5, HCH2Cp), 4.58 (2 H, s, br, HCH2Ar), 7.04-6.96 (1 H, m, ArH), 7.51-7.45 (2 H, m, ArH), 8.26-8.24 (1 H, m, ArH), 8.37 (1 H, s, br, ArH); δc (250 MHz, CDCl3) 156.32 (C), 156.01 (C), 149.29 (CH), 148.97 (CH), 139.85 (CH), 139.8 (C), 135.54 (CH), 133.81 ©, 123.51 (CH, 117.86 (C), 48.52 (CH2), 42.09 (CH2), 11.06 (CH3), 5.28 (2×(CH2); m/z 299.2 (M+H).
