Binap, (A+-)- → 5-(5-Bromo-4-(1-methylpiperidin-4-ylamino)pyridin-2-ylamino)pyrazine-2-carbonitrile

Participants

Reaction Conditions

Reaction Steps

A solution of 5-bromo-N4-(1-methylpiperidin-4-yl)pyridine-2,4-diamine (0.020 g, 0.070 mmol), 2-bromo-cyanopyrazine (0.013 g, 0.070 mmol), BINAP (0.002 g, 0.005 mmol), sodium tert-butoxide (0.009 g, 0.098 mmol), tris(dibenzylideneacetone)dipalladium chloroform complex (0.003 g, 0.003 mmol) in dioxane (0.5 mL was stirred at r.t. under nitrogen for 10 min before being heated for 6 h at 90° C. The crude reaction mixture was purified by ion exchange on SCX-II acidic resin (1 g) eluting with methanol/dichloromethane (1/1), then 2M ammonia-methanol. The basic fractions were combined and the solvent was removed in vacuo. The crude mixture was purified by preparative thin layer chromatography eluting with methanol/dichloromethane (1/9) to give the title compound as a yellow solid (0.002 g, 7%).

Provenance & Evidence