Triethylamine → HCID 178480823, compound

Participants

Reaction Steps

To a mixture of 2-[trans-4-(4-hydroxymethyl-phenyl)cyclohexyloxy]-1-methyl-1H-[4,4′]bipyrimidinyl-6-one (100 mg, 0.255 mmol) and triethylamine (51.6 mg, 0.510 mmol) in dichloromethane (1.3 ml) was added methanesulfonyl chloride (32.1 mg, 0.28 mmol) at 0° C. The mixture was warmed to room temperature and stirred overnight. The mixture was partitioned between water and dichloromethane. The organic layer was washed with brine, dried over sodium sulfate, and concentrated in vacuo. The residue was dissolved into tetrahydrofuran (1.3 ml) and N,N-dimethylformamide (0.3 ml). 1-Methylpiperazine (30.6 mg, 0.306 mmol) and potassium carbonate (52.8 mg, 0.382 mmol) was added to the solution. The mixture was stirred at 60° C. for 3 hours. The mixture was poured into water, and extracted with chloroform. The organic layer was washed with water (three times), dried over sodium sulfate, and concentrated in vacuo. The residue was purified by NH-silica gel column chromatography (eluent; ethyl acetate) to afford 1-methyl-2-{trans-4-[4-(4-methyl-piperazin-1-ylmethyl)phenyl]cyclohexyloxy}-1H-[4,4′]bipyrimidinyl-6-one as a colorless solid (51.1 mg, 0.108 mmol, 42%).

Provenance & Evidence