Hexane → HCID 178455249, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid (324) (350 mg, 0.79 mmol) in dimethylformamide (7.5 mL) were added [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amine (8i) (274 mg, 1.19 mmol) N,N-diisopropylethylamine (0.4 mL), 2.39 mmol) and HATU (364 mg, 0.96 mmol). The reaction mixture was stirred at room temperature for 1 h while silica thin layer chromatography was performed (ethyl acetate:hexane=1:1/UV/SiO2, Rf=0.5). The reaction mixture was diluted with ethyl acetate (60 mL), washed with brine (3×30 mL) and dried and concentrated in vacuo to get a crude mass of 5-benzyloxy-2-[1-(4-chlorophenyl)-cyclopentylmethyl]-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-cyclopropylmethyl-amide (329) (600 mg) which was used directly in the next step without further purification.

Provenance & Evidence