N,N-Dimethylglycine → 1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-5-[3-(trifluoromethyl)-1H-pyrazol-1-yl]-2,4(1H,3H)-pyrimidinedione

Participants

Reaction Conditions

Reaction Steps

5-iodo-1-(3-{(1S,5R)-1-[4-(trifluoromethyl)phenyl]-3-azabicyclo[3.1.0]hex-3-yl}propyl)-2,4(1H,3H)-pyrimidinedione (Prep10, 60 mg, 0.119 mmol), copper(1+) iodide (24.88 mg, 0.131 mmol), N,N-dimethylglycine (13.47 mg, 0.131 mmol) and K2CO3 (36.1 mg, 0.261 mmol) were dissolved in Dimethyl Sulfoxide (DMSO) (1 ml) to give a light blue suspension with a white solid. 3-(trifluoromethyl)-1H-pyrazole (commercially available from Apollo, 53.3 mg, 0.392 mmol) was added. After shaking at 150° C. for 18 h, the reaction mixture was diluted with EtOAc (5 ml) and the organic phase was washed with water (4×10 ml), then brine (5 ml), dried over Na2SO4, filtered ant the solvent evaporated. The obtained crude was purified by preparative LC-MS. Obtained 12.5 mg of the title compound.

Provenance & Evidence