4,6-Dichloropyrimidine → 4-Chloro-6-(2-chloro-imidazol-1-yl)-pyrimidine

Participants

Reaction Conditions

Reaction Steps

2-Chloro-1H-imidazole (2.0 g, 20 mmol), 4,6-dichloropyrimidine (6 g, 40 mmol) and DIEA (10.4 ml, 60 mmol) were mixed in 40 mL butanol and refluxed at 120° C. for 24 hours. The solvent was removed by rotary evaporation. The crude product was purified by flash chromatography on silica gel (0% EtOAc/hexanes to 20% EtOAc/hexanes gradient), afforded the title compound (2.6 g, 62% yield) as yellow solid. Rf=0.25 (20% EtOAc/hexanes); 1H NMR 400 MHz (DMSO-d6) δ 9.13 (s, 1H), 8.17 (s, 1H), 7.94 (d, 1H), 7.17 (d, 1 H); MS m/z 215.4 (M+1).

Provenance & Evidence