Diisopropylethylamine → HCID 178457474, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid (256) (0.5 g, 1.19 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (8b) (0.78 g, 3.58 mmol) in dry tetrahydrofuran (20.0 mL) were added propylphosphonic anhydride (0.76 g, 2.39 mmol, 50% in ethyl acetate) and diisopropyl ethylamine (0.8 mL, 4.78 mmol) at room temperature and the reaction mixture was heated at 65° C. for 4 h. After completion of the reaction, the mixture was portioned between ethyl acetate and water. The organic layer was separated, dried over Na2SO4 and concentrated under reduced pressure to get a crude product which was purified by normal silica gel column chromatography (using 30% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclohexylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (257) (0.25 g, 34.0%) as a colorless liquid.

Provenance & Evidence