Diisopropylethylamine → HCID 178484768, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (345) (300 mg, 0.66 mmol) in dimethylformamide (7.5 mL) were added N,N-diisopropylethylamine (0.33 mL, 1.98 mmol), [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amine (8a) (187 mg, 0.99 mmol) and HATU (301 mg, 0.79 mmol) and the reaction mixture was stirred at room temperature for 1.5 h (silica TLC, 50% ethyl acetate in hexane/SiO2/UV, Rf=0.6) The reaction mass was diluted with ethyl acetate (100 ml) and washed with brine (3×50 mL). The organic phase was thereafter dried and concentrated in vacuo to get a crude mass which was purified by Combi-Flash using a mixture of ethyl acetate and hexane as eluting solvent to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (350) (310 mg, 75%) as a light yellow sticky solid.

Provenance & Evidence