Hydrochloric Acid → HCID 178484637, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-methyl-amide (350) (280 mg, 0.45 mmol) in tetrahydrofuran (30.0 mL) was added 1N HCl (6.0 mL) at room temperature and the reaction mixture was stirred for 1 h at the same temperature (silica TLC, 5% methanol in dichloromethane, Rf=0.5). The tetrahydrofuran was removed under vacuum and the residue was diluted with water and extracted with ethyl acetate (2×25 mL). The organic layer was washed with NaHCO3 solution (10 mL), water (20 mL) and brine (20 mL). The organic layer was dried and concentrated in vacuum to get a crude mass which was purified by CombiFlash using gradient eluent of ethyl acetate and hexane mixture to get pure 5-benzyloxy-6-hydroxy-2-(1-naphthalen-1-yl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid (2-hydroxyethyl)-methyl-amide (351) (145 mg, 63%) as a white solid.

Provenance & Evidence