Sodium Carbonate → (4-{4-[1-Methyl-1-(methylsulfonyl)ethyl]-6-[(3S)-3-methylmorpholin-4-yl]pyrimidin-2-yl}phenyl)amine

Participants

Reaction Conditions

Reaction Steps

Dichlorobis(triphenylphosphine)palladium(II) (0.287 g, 0.41 mmol) was added to 2-chloro-4-[(3S)-3-methylmorpholin-4-yl]-6-(2-methylsulfonylpropan-2-yl)pyrimidine (2.73 g, 8.18 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.329 g, 10.63 mmol) and 2M aqueous sodium carbonate (15 mL, 29.44 mmol) in DMF (15 mL), DME (15 mL), ethanol (15 mL) and water (37.5 mL) at RT under nitrogen. The reaction was purged with nitrogen for 15 minutes and the resulting mixture was stirred at 80° C. for 3 hours. The reaction mixture was diluted with ethyl acetate (300 mL) and washed sequentially twice with water (150 mL) and saturated brine (150 mL). The organic layer was dried (MgSO4), filtered and evaporated to afford crude product as a dark brown gum. The crude product was purified by flash silica chromatography, eluting with 0 to 20% ethyl acetate in DCM, to give the desired material as a white solid (2.16 g).

Provenance & Evidence