Diisopropylethylamine → HCID 178455276, compound

Participants

Reaction Steps

To a stirred solution mixture of 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (283) (158 mg, 0.39 mmol) and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-oxetan-3-yl-amine (8 g) (104 mg, 0.47 mmol) in dimethylformamide (3 mL) were added N,N-diisopropylethylamine (0.2 mL, 1.17 mmol) and HATU (222 mg, 0.59 mmol). The reaction mixture was stirred at room temperature for 1 h, followed by the addition of water (50 mL). the mixture was extracted with ethyl acetate (3×20 mL) and 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]-oxetan-3-yl-amide (296) (240 mg, 99.43%) as a yellow gummy mass.

Provenance & Evidence