3-[(4-methoxyphenyl)methoxy]propan-1-ol

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of 7-cycloheptyl-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol (362 mg, 1.0 mmol) and 3-[(4-methoxybenzyl)oxy]-1-propanol (490 mg, 2.5 mmol) in 4.0 mL of dimethylsulfoxide at room temperature is added sodium hydride (60% in mineral oil, 120 mg, 3.0 mmol). The mixture is stirred at room temperature for 3 h, and partitioned between ethyl acetate and 1.0 N hydrochloric acid. The organic solution is washed with saturated sodium chloride, dried over magnesium sulfate, and concentrated to a residue. The residue is chromatographed over silica gel, eluting with a gradient of 66% ethyl acetate in hexanes to 5% methyl alcohol in ethyl acetate. Concentration provides 7-cycloheptyl-6-(2,6-difluoro-4-{3-[(4-methoxybenzyl)oxy]propoxy}phenyl)[1,2,4]triazolo[1,5-a]pyrimidin-5-ol as a yellow oil (820 mg). partitioned between ethyl acetate and 1.0 N hydrochloric acid The organic solution is washed with saturated sodium chloride dried over magnesium sulfate concentrated to a residue The residue is chromatographed over silica gel eluting with a gradient of 66% ethyl acetate in hexanes to 5% methyl alcohol in ethyl acetate Concentration