Diisopropylethylamine → HCID 178425124, compound

Participants

Reaction Steps

To a stirred solution of 6-chloro-2-fluoropurine (0.4 g, 2.3 mmol) in n-BuOH (50 ml) under an argon atmosphere at 0° C., was added DIEA (2.5 ml, 14.7 mmol) followed by (6-methylpyridin-2-yl)methanamine (0.36 g, 2.95 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, it was still seen incomplete, hence heated the reaction to 100° C. and left at that temperature for 8 h. 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: 0.35 g (60%). δH (CDCl3, 500 MHz) 2.44 (3 H, s, CH3), 4.83-4.54 (3 H, m, NH and NHCH2), 7.1-7.05 (2 H, m, ArH), 7.61-7.55 (1 H, m, ArH), 8.13-8.09 (1 H, m, ArH), 8.61 (1 H, s, br, NH); δC (CDCl3, 500 MHz) 159.41 (C), 158.78 (C), 158.53 (C), 157.19 (C), 155.38 (C), 147.69 (CH), 137.03 (C), 136.93 (CH), 121.34 (CH), 117.76 (CH), 117.31 (C), 46.47 (CH2), 23.9 (CH3); m/z 259.2 (M+H)

Provenance & Evidence