Sodium Methoxide → HCID 178450818, compound

Participants

Reaction Steps

To a stirred solution of 2-biphenyl-2-yl-acetamidine acetate salt (5-01) (2.5 g, 9.2 mmol) and (E)-2-benzyloxy-3-hydroxy-but-2-enedioic acid 4-tert-butyl ester 1-methyl ester (4) (4.2 g, 13.88 mmol) in methanol (60 mL) was added sodium methoxide (1.5 g, 27.77 mmol) at 0° C., then the reaction mixture was allowed to warm to room temperature and was stirred for 16 h. After completion of the reaction, it was quenched with 1N HCl, evaporated and w ater was added. The mixture was extracted with ethyl acetate and the separated organic part was dried over sodium sulfate and concentrated under reduced pressure to get a crude product, which was purified using a normal silica column using 30% ethyl acetate in hexane to get 5-benzyloxy-2-biphenyl-2-ylmethyl-6-hydroxypyrimidine-4-carboxylic acid tert-butyl ester (6-01) (2.5 g, 57.63%) as a white solid.

Provenance & Evidence