Phosphorus oxychloride → HCID 178457489, compound

Participants

Reaction Conditions

Reaction Steps

N-(2-(tert-Butyldimethylsilyloxy)ethyl)propan-2-amine (8b) (98.0 mg, 451 μmol, Eq: 1.1, prepared as previously described) was added to 5-(benzyloxy)-6-hydroxy-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxylic acid (56) (155 mg, 410 μmol, Eq: 1.00), then pyridine (2.5 ml) was added, and the reaction mixture was cooled to −10° C. with stirring. POCl3 (188 mg, 115 μl, 1.23 mmol, Eq: 3) was added dropwise, then the reaction mixture was stirred at −10° C. for 1 hour, allowed to warm to 0° C. and stirred for one hour. 10 drops of water were added at 0° C., the reaction mixture was stirred for 5 min and the solvent was removed on a rotary evaporator to almost dryness. The mixture was placed on 12 g silica gel column and eluted with 5% to 50% ethyl acetate/hexane over 20 min. to give 5-(benzyloxy)-N-(2-(tert-butyldimethylsilyloxy)ethyl)-6-hydroxy-N-isopropyl-2-(2-methyl-2-phenylpropyl)pyrimidine-4-carboxamide (57) (62 mg, 26%).

Provenance & Evidence