m-Toluidine → HCID 68205816, compound

Participants

Reaction Steps

3-chloro-N-methylpyrazin-2-amine (6 g, 41.8 mmol), m-toluidine (6.72 g, 62.7 mmol), 2,2′-bis(diphenylphosphino)-1,1′-binaphthalene (0.520 g, 0.836 mmol), Pd2(dba)3 (0.383 g, 0.418 mmol), and sodium t-butoxide (6.02 g, 62.7 mmol) were mixed in 200 mL of toluene and degassed for 20 minutes. The mixture was heated to reflux overnight. TLC indicated the reaction did not go to completion. 0.3 g of Pd2(dba)3 and 0.56 g of BINAP was added and heated up to reflux again for 24 h. The reaction was filtered through Celite® and concentrated. The residue was purified by column using 10% ethyl acetate and dichloromethane as solvent to give N2-methyl-N3-(m-tolyl)pyrazine-2,3-diamine (2.7 g, 30.2%).

Provenance & Evidence