4-Hydroxymethylpyridine → HCID 19787879, compound

Participants

Reaction Steps

To a solution of 2-(5-amino-6-oxo-2-phenyl-1,6-dihydro-1-pyrimidinyl)-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide (1.1 g) and triphosgene (0.93 g) in dichloromethane at 0° C. was added triethylamine (2.0 mL) and the resulting solution was allowed to stir for 0.5 h. To this solution was added 4-pyridylcarbinol and the resulting solution allowed to stir overnight. The solution was poured into saturated aqueous sodium bicarbonate solution and the product was extracted into dichloromethane. The organic solution was washed (saturated aqueous sodium bicarbonate, water), dried, and evaporated. The resulting oil was purified by chromatography, with methanol:dichloromethane (5:95) as the eluent, to provide 2-[6-oxo-2-phenyl-5-(4-pyridylmethoxycarbonylamino)-1,6-dihydro-1-pyrimidinyl]-N-(2-tert-butyldimethylsilyloxy-3,3,3-trifluoro-1-isopropylpropyl)acetamide as a white solid (0.9 g); TLC: Rf =0.4, methanol:dichloromethane (5:95).

Provenance & Evidence