Lithium Hexamethyldisilazide → HCID 68848147, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred suspension of 2-[4-(methylsulfonyl)piperazin-1-yl]-5-(2,2,2-trifluoroethoxy)pyrimidine (8.05 g, 23.6 mmol) in THF (175 mL) at −78° C. was added LHMDS (47.2 mL, 47.2 mmol) dropwise and the reaction stirred for 15 minutes. A solution of ethyl 4-pyrimidin-2-ylbutanoate (5.5 g, 28.3 mmol) in THF (50 mL) was then added at −78° C., warmed to −20° C. and stirred for 2 hours. The reaction was then quenched by addition of a saturated solution of NH4Cl (250 mL), extracted twice with EtOAc (2×250 mL), combined organics were washed with brine (250 mL), dried (MgSO4), filtered and concentrated in vacuo to give a yellow solid. This was then purified by flash chromatography (silica gel, 50% EtOAc/hexanes) to give 5-pyrimidin-2-yl-1-({4-[5-(2,2,2-trifluoroethoxy)pyrimidin-2-yl]piperazin-1-yl}sulfonyl)pentan-2-one as an off white solid (9.47 g, 19.4 mmol, 82%).

Provenance & Evidence