Diisopropylethylamine → HCID 178455281, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-pyridin-2-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (437) (150 mg, 0.494 mmol) in dimethylformamide (5 mL), N,N-diisopropylethylamine (0.184 mL, 1.111 mmol), HATU (211.24 mg, 0.556 mmol) and [2-(tert-Butyl-dimethylsilanyloxy)-ethyl]-cyclopropyl-amine (crude) (8d) (239 mg) were added. 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 (25 mL) and extracted with ethyl acetate (2×30 mL). The organic part was dried, then concentrated and the 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]-cyclopropyl-amide (450) (120 mg, 54%) as a yellow sticky liquid.

Provenance & Evidence