Benzenemethanamine, 3-chloro- → HCID 178506014, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 6-chloro-2-fluoropurine (1 g, 1 eq, 5.9 mmol) in n-BuOH (50 ml) under an argon atmosphere, was added DIEA (2.6 ml, 2.5 eq, 14.75 mmol) followed by 3-chloro-benzylamine (1.25 g 1.5 eq, 8.85 mmol). The reaction mixture was heated at 100° C. for 3 hours after which the reaction was complete. The solvent was evaporated in vacuo and the residue purified by gradient column chromatography on silica gel, eluted with DCM:ether:MeOH (55:45:0→55:43:2), to afford the title compound as a white solid; Yield: 1.15 g (70%). δH (250 MHz, d6-DMSO) 4.78-4.6 (2 H, m, NHCH2Ar), 7.41-7.28 (4 H, m, ArH), 7.57 (1 H, s, br, ArH), 8.15 (1 H, s, br, NH), 8.88 (1 H, s, br, NH); δC (250 MHz, d6-DMSO) 142.3 (C), 133.02 (C), 132.92 (C), 130.25 (CH), 130.17 (C), 127.82 (CH), 127.27 (CH), 127.03 (CH), 126.76 (C), 125.92 (CH), 116.4 (C), 115 (C), 42.67 (CH2); m/z 278 (M+H)

Provenance & Evidence