Sodium Carbonate → HCID 59380168, compound

Participants

Reaction Conditions

Reaction Steps

Dichlorobis(triphenylphosphine)palladium(II) (0.360 g, 0.51 mmol) was added to a degassed solution of 2-chloro-4-(2-ethylsulfonylpropan-2-yl)-6-[(3S)-3-methylmorpholin-4-yl]pyrimidine (1.784 g, 5.13 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (1.404 g, 6.41 mmol) and sodium carbonate (12.82 mL, 25.64 mmol) in a mixture of 18% DMF in DME:water:ethanol (7:3:2) (25 mL). The resulting solution was stirred at 85° C. for 2 hours. The reaction mixture was concentrated and partitioned between DCM (150 mL), and water (100 mL) and the organics washed with brine (100 mL), dried (MgSO4), filtered and evaporated to afford crude product. The crude product was purified by flash silica chromatography, elution gradient 0 to 2.5% methanol in DCM, to give the desired material as a brown solid (1.20 g).

Provenance & Evidence