Diisopropylethylamine → HCID 178457480, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (437) (180 mg, 0.44 mmol) in dimethylformamide (5 mL), N,N-diisopropylethylamine (0.22 mL, 1.33 mmol), HATU (253.5 mg, 0.667 mmol), and [2-(tert-Butyl-dimethylsilanyloxy)-ethyl]-isopropyl-amine (8b) were added, then this reaction mixture was allowed to stir for 16 h at room temperature while silica thin layer chromatography was performed (50% ethyl acetate in hexane; Rf=0.5). The reaction was quenched with ice cold water (20 mL) and extracted with ethyl acetate (2×30 mL). The combined extracts were dried, concentrated under vacuo and the resulting crude product was purified by normal 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-carboxylicacid[2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (438) (160 mg, 60%) as a yellow gummy liquid.

Provenance & Evidence