Tributyltin Chloride → 4-Methyl-2-(4-tributylstannanyl-imidazol-1-yl)-6-(4-trifluoromethyl-phenyl)-pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 2-(4-iodo-imidazol-1-yl)-4-methyl-6-(4-trifluoromethyl-phenyl)-pyrimidine (Example E.71) (0.43 g, 1.0 mmol) in THF (7 mL) was added at 0° C. iso-propylmagnesium chloride lithium chloride (1M in THF, 1.22 mL, 1.22 mmol). The reaction mixture was allowed to stir for 15 min at 0° C., tributyltin chloride (0.43 g, 1.33 mmol) was added, the reaction mixture was stirred at room temperature for 5 h, poured into saturated ammonium chloride solution (30 mL) and extracted with ethyl acetate (2×50 mL). The combined organic layers were washed with brine (30 mL), dried (MgSO4) and evaporated. The crude product was further purified by flash chromatography on silica gel (ethylacetate/heptane) to yield the title compound (0.55 g, 93%) as a light yellow oil. MS (ISP) 595.3 [(M+H)+].

Provenance & Evidence