tert-butyl N-[(4-hydroxyphenyl)methyl]carbamate

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

Procedure: 60% Sodium hydride (394 mg) was suspended in 1,2-dimethoxyethane (20 mL), and tert-butyl 4-hydroxybenzylcarbamate (1 g) and 15-crown-5-ether (1.09 g) were added thereto, followed by stirring at room temperature for 30 minutes. 4,6-Dichloro-2-(methylsulfonyl)pyrimidine was added thereto, followed by stirring at 80° C. overnight. The reaction solution was cooled to room temperature and then an aqueous ammonium chloride solution (50 mL) was added thereto, followed by extraction with ethyl acetate. The extracts were washed with water and saturated brine, and the organic layer was dried over anhydrous magnesium sulfate. The desiccant was removed by filtration and the solvent was evaporated under reduced pressure. The residue was purified using silica gel column chromatography (hexane:ethyl acetate=95:5-85:15) to obtain tert-butyl{-4-[(4,6-dichloropyrimidin-2-yl)oxy]benzyl}carbamate (762 mg). by stirring at 80° C. overnight The reaction solution was cooled to room temperature followed by extraction with ethyl acetate The extracts were washed with water and saturated brine the organic layer was dried over anhydrous magnesium sulfate The desiccant was removed by filtration the solvent was evaporated under reduced pressure The residue was purified