Tetrahydrofuran → Methyl 4,4-dimethyl-2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)pentanoate

Participants

Reaction Conditions

Reaction Steps

To a cooled (−15° C.) solution of methyl 2-(4-methyl-2-(piperidin-1-yl)-6-p-tolylpyrimidin-5-yl)acetate (0.200 g; 0.589 mmol) in a mixture of dry DMF (1.2 mL) and HMPA (0.3 mL) was wadded a 1N solution of KHMDS in THF (0.825 mL; 0.825 mmol) dropwise and the mixture was stirred at (−15° C.) for 15 min, followed by the dropwise addition of 1-iodo-2,2-dimethylpropane (0.313 mL; 2.357 mmol). After stirring for 1 h at (−15° C.) the mixture was allowed to warm up to room temperature and stirring was carried on 4 h. The reaction was quenched by adding a saturated solution of ammonium chloride and the mixture was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate, filtered and concentrated under reduced pressure. Purification by flash-chromatography on silica gel using a gradient of ethyl acetate (2-20%) in heptane furnished 0.024 g (9%) of the title compound.

Provenance & Evidence