Dimethylformamide → 3-[2-(Methylthio)-4-pyrimidinyl]-2-(3-nitrophenyl)-5-[(phenylmethyl)oxy]-pyrazolo[1,5-a]pyridine

Participants

Reaction Conditions

Reaction Steps

A solution of 1-amino-4-[(phenylmethyl)oxy]pyridinium 2,4,6-trimethylbenzenesulfonate (13.8 mmol; crude) and 2-(methylthio)-4-[(3-nitrophenyl)ethynyl]pyrimidine (6.30 g, 9.22 mmol) in dry-DMF (70 mL) was cooled to 0° C. Aq. K2CO3 (2.75 mL, 18.4 mmol) was added. The mixture was stirred at rt overnight. The reaction mixture was poured into water and extracted with EtOAc. The organic phase was combined, washed with brine, and dried (MgSO4). The solvent was evaporated under reduced pressure. Chromatography on silica gel eluting with hexane/EtOAc gradient (15-50% EtOAc) gave yellow solid (460 mg).

Provenance & Evidence