2,6-Dichloropyrazine → 6-chloro-N-(4-methylsulfonylphenyl)pyrazin-2-amine

Participants

Reaction Conditions

Reaction Steps

2,6-dichloropyrazine (287 mg, 1.93 mmol), 4-(methylsulfonyl)aniline (330 mg, 1.93 mmol), diacetoxypalladium (43.3 mg, 0.19 mmol), 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl (120 mg, 0.19 mmol) and cesium carbonate (690 mg, 2.12 mmol) in 1,4-dioxane (2 mL) were degazed and stirred at 90 °C for 16 hours under nitrogen. The reaction mixture was evaporated to dryness and was purified by preparative HPLC using a Waters SunFire reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml / minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford 6-chloro-N-(4-(methylsulfonyl)phenyl)pyrazin-2-amine (120 mg, 21.95 %) as a yellow solid.

Provenance & Evidence