Toluene → HCID 66750107, compound

Participants

Reaction Steps

A mixture of 3-(2-chloro-6-phenylpyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane (500 mg, 1.66 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (545 mg, 2.49 mmol), Pd(PPh3)4 (20 mg), and 2M aqueous Na2CO3 (1.25 mL) in 1:1 toluene:EtOH (8 mL) was heated in a microwave at 120° C. for 20 min. The reaction was repeated with 386 mg of 3-(2-chloro-6-phenylpyrimidin-4-yl)-8-oxa-3-azabicyclo[3.2.1]octane. The reaction mixtures were combined, diluted with EtOAc and washed with H2O then brine. The organic layer was dried over MgSO4 and concentrated in vacuo to give an orange oil. Silica gel chromatography (hexane/EtOAc) gave 4-(4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-phenylpyrimidin-2-yl)aniline as a white solid (450 mg).

Provenance & Evidence