4-[6-(2-Benzyloxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester → Piperidine-4-carboxylic acid [6-(2-benzyloxy-phenyl)-pyrimidin-4-yl]-amide

Participants

Reaction Steps

4-[6-(2-Benzyloxy-phenyl)-pyrimidin-4-ylcarbamoyl]-piperidine-1-carboxylic acid benzyl ester (XVI) (0.5 g, 1 mmol) was dissolved in 33% HBr in acetic acid (3 ml) and stirred at room temperature for 45 minutes. A yellow solid precipitated out; the reaction mixture was quenched at 0° C. with aqueous sodium hydroxide solution and extracted with ethyl acetate (3×10 ml). The organic phases were separated, combined, dried over sodium sulfate and concentrated under reduced pressure. The crude product was purified by preparative HPLC (C-18, AcN:H2O with 0.05% TFA) and lyophilized to afford piperidine-4-carboxylic acid [6-(2-benzyloxy-phenyl)-pyrimidin-4-yl]-amide (compound #9A) (0.028 g, 7%) as a white solid.

Provenance & Evidence