Sodium Methoxide → HCID 178450806, compound

Participants

Reaction Steps

To a stirred solution of 2-(1-phenyl-cyclopentyl)-acetamidine hydrochloride salt (281) (500 mg, 2.09 mmol) and (E)-3-benzyloxy-2-hydroxy-4-oxo-pent-2-enoic acid tert-butyl ester (4) (970 mg, 3.15 mmol) in methanol (10 mL) was added a sodium methoxide solution (25% in methanol) (1.4 mL, 6.29 mmol) at 0° C. and then the reaction mixture was allowed to warm slowly up to room temperature while stirring was continued for 16 h. After completion of the reaction, the reaction mixture was quenched with 1N HCl (5 mL) and the methanol was evaporated and water (20 mL) was added. The mixture was extracted with ethyl acetate (3×20 mL) and the phases separated. The organic part was dried and concentrated to get a crude product, which was purified by Combi-Flash column (eluted at 10-20% ethyl acetate in hexane) to obtain 5-benzyloxy-6-hydroxy-2-(1-phenyl-cyclopentylmethyl)-pyrimidine-4-carboxylic acid tert-butyl ester (282) (230 mg, 23.82%) as a white solid.

Provenance & Evidence