Benzyl Alcohol → HCID 18932925, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-allyl-2-phenylpyrimidin-6(1H)-one-5-carboxylic acid (30.2 g) and triethylamine (32.8 mL) in dioxane (390 mL) was added diphenylphosphoryl azide (25.6 mL), and the resulting solution was heated at 100° C. for 2 h. Benzyl alcohol (24.5 mL) was added and the resulting solution was heated at 100° C. for 12 h. The solution was cooled and the solvent evaporated. The resulting residue was dissolved in ethyl acetate, washed (saturated ammonium chloride, 1N sodium hydroxide, water), dried, and evaporated to give an oil which crystallized upon addition of ether to give a white solid. The solid was collected and washed with ether to provide 1-allyl-5-benzyloxycarbonylamino-2-phenylpyrimid-6(1H)-one (25.1 g); 300 MHz NMR: 8.93 (s,1), 8.45 (s,1), 7.43 (m,10), 5.75 (m,1), 5.18 (s,2), 5.08 (d,1), 4.82 (d,1), 4.46 (d,2).

Provenance & Evidence