Cesium carbonate → HCID 67981041, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of benzyl 5-carbamoylbicyclo[3.2.1]octan-1-ylcarbamate (1 g, 3.3 mmol) and Cs2CO3 (1.6 g, 4.9 mmol) and BINAP (200 mg, 0.3 mmol) in toluene (60 mL), was added 4-chloro-2-methylpyrimidine (430 mg, 3.3 mmol), followed by Pd2(dba)3 (300 mg, 0.32 mmol). The mixture was stirred at 100° C. under N2 overnight. After cooled to room temperature, the reaction mixture was concentrated under reduced pressure and the resulting residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate: 4/1) to give 1 g (77%) of benzyl 5-(2-methylpyrimidin-4-ylcarbamoyl)bicyclo[3.2.1]octan-1-ylcarbamate as a light yellow oil. ESI-MS m/z: 395 (M+H)+.

Provenance & Evidence