Sodium Iodide → 1-(4-Trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)-1-benzyloxymethane

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Reaction Steps

1-(4-trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)methanol (56 mg, 0.196 mmol) in THF (2.5 ml) was added dropwise to a suspension of NaH (12 mg, 0.40 mmol, 80% in mineral oil) in THF (0.5 ml) at ice-bath temperature and stirred for 45 minutes. NaI (56 mg, 0.37 mmol) was then added as a solid and benzyl chloride (50 μl, 54 mg, 0.90 mmol, 2.25 equivalent) via syringe. Dimethyl formamide (DMF) (0.5 ml) was added and the solution was allowed to warm to room temperature. When the reaction was complete, as determined by TLC (SiO2 ; hexane/EtOAc, 1:1), it was quenched with 30% aqueous HOAc, diluted with water and extracted with EtOAc (3 times). The combined extracts were washed with brine (sat.), dried (MgSO4), filtered and concentrated in vacuo to give 66 mg of crude material. Preparative thin layer chromatography (SiO2 ; hexane/EtOAc, 1:1) afforded 39 mg of 1-(4-trifluoromethylpyrimidin-5-yl)-1-(4-methoxypyrimidin-5-yl)-1-benzyloxymethane as an oil.

Provenance & Evidence