Diisopropylethylamine → HCID 178455275, compound

Participants

Reaction Steps

To a stirred solution mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (400 mg, 0.99 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-(tetrahydro-pyran-4-yl)-amine (8j) (513 mg, 1.98 mmol) in dimethylformamide (6 mL) were added N,N-diisopropylethylamine (0.5 mL, 2.97 mmol) and HATU (564 mg, 1.48 mmol). Stirring was continued at room temperature for 1 h. Water (75 mL) was added and the mixture was extracted with ethyl acetate (3×20 mL). The combined organic part was washed with water (3×50 mL) and brine (2×30 mL) and dried and concentrated. The crude product was purified by Combi-Flash column (eluted at 20-30% ethyl acetate in hexane) to get 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-(tetrahydro-pyran-4-yl)-amide (308) (540 mg, 84.53%) as a colorless sticky solid.

Provenance & Evidence