3-chloro-N-isopropylpyrazin-2-amine (6 g, 35.0 mmol), m-toluidine (5.62 g, 52.4 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.435 g, 0.699 mmol), Pd2(dba)3 (0.320 g, 0.350 mmol), and sodium t-butoxide (5.04 g, 52.4 mmol) were mixed in 200 mL of toluene and degassed for 20 minutes. The mixture was heated to reflux for 5 h. The reaction was cooled to room temperature and water was added. The reaction mixture was extracted with dichloromethane and washed with water. The crude was columned with 10% ethyl acetate and dichloromethane to give N2-isopropyl-N3-(m-tolyl)pyrazine-2,3-diamine (7.4 g, 87%).
