Ethyl Acetate → HCID 178457452, compound

Participants

Reaction Steps

To a stirred solution of 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylic acid [2-(tert-butyl-dimethylsilanyloxy)-ethyl]-isopropylamide (378) (5.7 g, 8.80 mmol) in tetrahydrofuran (50 mL), 1N HCl (15 mL) was added and the reaction mixture was stirred for 1 h at room temperature while silica thin layer chromatography was performed (70% ethyl acetate in hexane; Rf=0.2). After completion of the reaction, volatiles were removed and the residue was diluted with water (30 mL) and adjusted to pH 8 using NaHCO3. The aqueous mixture was extracted with ethyl acetate (2×150 mL) and the combined extracts were dried and concentrated. The resulting residue was purified by column over normal silica gel (100-200) to get 5-benzyloxy-2-(2-bromo-4-chlorobenzyl)-6-hydroxypyrimidine-4-carboxylicacid(2-hydroxyethyl)-isopropylamide (379) (4.02 g, 85.45%) as a white solid.

Provenance & Evidence