Dimethylformamide → HCID 59564548, compound

Participants

Reaction Steps

2-(4-Morpholino)pyrimidine-5-boronic acid pinacol ester (300 mg, 1.03 mmol), 1,2-dibromobenzene (243 mg, 1.03 mmol), Bis(triphenylphosphine)palladium (II) chloride (72 mg, 0.10 mmol), aqueous Na2CO3 (2N, 2.58 mL, 5.15 mmol) and DMF (5 mL) are added to a 10 mL microwave tube. Reaction is carried out in a microwave oven at 100° C. for 30 min. The reaction mixture turns black. The mixture is poured into water and extracted with EtOAc. The organic layers are washed with water, brine, dried (Na2SO4) and concentrated. The crude product is purified using biotage eluting with 0-30% EtOAc/Hexane. The desired mono-coupled product elutes at 30% EtOAc. The di-coupled by-product elutes earlier. Removal of the solvent gives 4-[5-(2-bromo-phenyl)-pyrimidin-2-yl]-morpholine as a white solid (130 mg, 39%).

Provenance & Evidence