Diisopropylethylamine → HCID 178484771, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (437) (200 mg, 0.494 mmol) in dimethylformamide (7 mL), N,N-diisopropylethylamine (0.245 mL, 1.481 mmol), HATU (281.7 mg, 0.741 mmol). and [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amine (8a) were added. This reaction mixture was allowed to stir for 16 h at room temperature while silica thin layer chromatography was performed (70% ethyl acetate in hexane, Rf=0.5). The reaction mixture was quenched with ice cold water (20 mL) and extracted with ethyl acetate (2×50 mL). The organic part was dried and concentrated. The resulting crude product was purified by nor mal silica gel (100-200 mesh) column chromatography using 30-40% ethyl acetate in hexane as gradient polarity mobile phase to get 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (442) (220 mg, 77%) as a yellow gummy liquid.

Provenance & Evidence