Cesium carbonate → (1S,6R)-Benzyl 3-(4,6-dimethylpyrimidin-2-yl)-3,8-diazabicyclo[4.2.0]octane-8-carboxylate

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Reaction Conditions

Reaction Steps

To (1S,6R)-benzyl 3,8-diazabicyclo[4.2.0]octane-8-carboxylate (2.5 g, 6.9 mmol) and 2-chloro-4,6-dimethylpyrimidine (980 mg, 6.9 mmol) in DMF (35 mL) was added Cs2CO3 (9.0 g, 27.6 mmol). The reaction flask was heated to 100° C. until starting materials were consumed, cooled to rt, diluted with EtOAc and washed with H2O. The aqueous layer was back-extracted with EtOAc (1×). The combined organics were washed with brine and dried (Na2SO4) to give an oil. Purification via silica gel (15-75% EtOAc in hexanes) gave 1.6 g (63%) of the title compound as a clear oil. MS (ESI) mass calcd. C20H24N4O2, 352.44; m/z found 353.2 [M+H]+.

Provenance & Evidence