Diisopropylethylamine → HCID 178455268, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (345) (250 mg, 0.55 mmol) in dimethylformamide (7.5 mL) were added N,N-diisopropylethylamine (0.27 mL, 1.65 mmol), 2-(tert-butyl-dimethylsilanyloxy)-ethylamine (8c) (145 mg, 0.83 mmol) and HATU (251 mg, 0.66 mmol) and the reaction mixture was stirred at room temperature for 1.5 h (silica TLC, 50% ethyl acetate in hexane, Rf=0.5). The reaction mass was diluted with ethyl acetate (60 ml) and washed with brine (3×30 mL). The organic phase was thereafter dried and concentrated in vacuo to get a crude mass which was purified by CombiFlash using a gradient eluent mixture of ethyl acetate and hexane to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-amide (346) (315 mg, 94%) as a white solid.

Provenance & Evidence