1-Butanol → N-((2-(3-fluoro-phenyl)-8-methoxyquinolin-3-yl)methyl)-9H-purin-6-amine

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-bromopurine (0.1418 g, 0.7125 mmol), (2-(3-fluorophenyl)-8-methoxyquinolin-3-yl)methanamine (0.2213 g, 0.7838 mmol), and N,N-diiso-propylethylamine (0.2482 mL, 1.425 mmol) in 1-butanol (7.125 mL, 0.7125 mmol) was stirred at 100° C. After 24 h, the mixture was removed from the heat and concentrated under reduced pressure. The residue was purified by flash column chromatography on a silica gel column using 50% of CH2Cl2:MeOH:NH4OH (89:9:1) in CH2Cl2 as eluent to give an off-white solid. The off-white solid was suspended in EtOAc and filtered to give N-((2-(3-fluoro-phenyl)-8-methoxyquinolin-3-yl)methyl)-9H-purin-6-amine as a white solid: 1H NMR (400 MHz, DMSO-d6) δ ppm 12.95 (1 H, s), 8.18-8.30 (2 H, m), 8.11 (2 H, s), 7.42-7.61 (5 H, m), 7.28-7.36 (1 H, m), 7.16 (1 H, dd, J=7.1, 1.7 Hz), 4.71-4.95 (2 H, m), 3.95 (3 H, s); LC-MS (ESI) m/z 401.2 [M+H]+.

Provenance & Evidence