Methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)pentanoate → Methyl 2-(2-benzyl-4-methyl-6-phenylpyrimidin-5-yl)pentanoate

Participants

Reaction Steps

THF (4 ml) was added to an argon purged glass tube (20 mL) containing methyl 2-(2-chloro-4-methyl-6-phenylpyrimidin-5-yl)pentanoate (135 mg; 0.423 mmol) and tetrakis(triphenylphosphine) palladium(0) (24.47 mg; 0.021 mmol). The mixture was stirred at room temperature for 10 min and, after dissolution of the solids, benzylzinc bromide (1.694 ml; 0.847 mmol; 0,5 M in THF) was added dropwise. Stirring at room temperature was continued for 15 min followed by stirring at 60° C. for 8 h. The reaction was quenched by adding a saturated ammonium chloride solution. To this suspension was added a saturated disodium ethylenediamine tetraacetate solution and the mixture was stirred at room temperature for 15 min. The mixture was extracted twice with ethyl acetate and the organic layers were washed with brine and dried over magnesium sulphate. The crude material was purified by flash chromatography on silica gel using a linear gradient of ethylacetate (2-20%) in heptane to give 101 mg (64%) of the title compound. ESI/APCI(+): 375 (M+H). ESI/APCI(−): 373 (M−H).

Provenance & Evidence