1-Iodopropane → Methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)pentanoate

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 2-(2-chloro-4-methyl-6-p-tolylpyrimidin-5-yl)acetate (2.5 g; 8.60 mmol) in dry DMF (40 mL) was cooled to −78° C. LHMDS (9.46 mL; 9.46 mmol; 1M in THF) was added dropwise and the mixture was stirred at −78° C. for 15 min followed by the dropwise addition of iodopropane (1.260 ml; 12.90 mmol). After stirring for 2 h at −15° C. the mixture was allowed to warm up to room temperature. After 1 h the reaction was quenched by adding a saturated solution of ammonium chloride. The mixture was extracted twice with ethyl acetate and the combined organic layers were washed with brine, dried over magnesium sulphate and concentrated under reduced pressure. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-10%) in heptane to give 1.131 g (37%) of the title compound as a yellow oil. ESI/APCI(+): 333 (M+H).

Provenance & Evidence