Water → HCID 86669618, compound

Participants

Reaction Steps

To a solution of 2-chloropyrimidin-4-amine (1.31 g, 10.08 mmol) in THF (55 mL) at 0° C. was added sodium hydride (60% in oil, 806.69 mg, 20.17 mmol) portion-wise. The reaction mixture was stirred at 0° C. to RT for 10 minutes and 1-bromo-2,5-difluoro-4-nitrobenzene (1.2 g, 5.04 mmol) was added. The reaction mixture was stirred at 65° C. for 1 h. The reaction mixture was cooled to RT and water (30 mL) was added. Product extracted into DCM (2×30 mL) and washed with water (20 mL). The combined organics were dried (Na2SO4), filtered and concentrated in vacuo. The crude product was purified by column chromatography (Biotage) eluted with DCM:MeOH gradient (99:1 to 95:05) to afford the title compound as an orange solid (1005 mg, 56% yield); 1H NMR (250 MHz, DMSO) delta 6.87 (1H, d, J=5.83 Hz), 8.08 (1H, d, J=6.31 Hz), 8.18 (1H, d, J=8.35 Hz), 8.27 (1H, d, J=5.83 Hz), 10.32 (1H, br. s.); LC-MS: m/z+348.70 (M+H)+.

Provenance & Evidence