Chloroform → HCID 178506017, compound

Participants

Reaction Steps

To a stirred solution of 6-chloro-2-fluoropurine (1 g, 5.8 mmol) in n-BuOH (50 mL) under an argon atmosphere at 0° C., was added diisopropylethylamine (3 ml, 17.4 mmol) followed by 4-(aminomethyl)pyridine (0.9 ml, 1.5 eq, 8.7 mmol). The reaction mixture was stirred at this temperature for 1 h and then allowed to return to room temperature and stirred for 4 h, when TLC(CHCl3:MeOH; 90:10) indicated that the reaction had gone to completion. The solvent was evaporated in vacuo and the residue was purified by gradient flash column chromatography on silica gel, eluted with CHCl3:MeOH (100:0→90:10), to afford the product as a white solid; Yield: 0.85 g (60%). mp 200-202° C. 1H-NMR (d6-DMSO, 250 MHz): δ 4.67 (2 H, d, J 5, —HNCH2-Pyr), 7.34-7.28 (2 H, m, Pyr-H), 8.48-8.42 (2 H, m, Pyr-H), 8.54 (1 H, s, —N═CH—NH—), 8.84 (1 H, s, br, —HNCH2-Pyr), 13.13 (1 H, s, b, —N═CH—NH—); m/z 245 ([M+H]+

Provenance & Evidence