Diisopropylethylamine → HCID 178426369, compound

Participants

Reaction Steps

To a stirred solution of 6-chloro-2-fluoropurine (0.4 g, 2.9 mmol) in n-BuOH (50 ml) under an argon atmosphere at 0° C., was added DIEA (2.5 ml, 14.7 mmol) followed by (2,6-dimethylpyridin-4-yl)methanamine (0.54 g, 4 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: 0.5 g (63%); δH CDCl3, 250 MHz) 2.48 (6H, s, 2×CH3), 3.65-3.54 (2 H, m, NHCH2), 4.61 (1 H, s, br, NH), 7.32 (2 H, s, ArH), 7.84 (1 H, s, ArH)), 9.05 (1 H, s, br, NH); δC (CDCl3, 250 MHz) 159.2 (C), 156.62 (C), 156.61 (C), 155.46 (C), 146.92 (CH), 136.3 (C), 122.05 (2×CH), 119.48 (C), 41.6 (CH2), 18.06 (2×CH3)

Provenance & Evidence