Dimethyl Sulfide → 7-Oxo-5,6,7,8-tetrahydropyrido[2,3-d]pyrimidine-2-carbaldehyde

Participants

Reaction Steps

To a round bottom flask was added 2-[(E)-2-phenylethenyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (600 mg, 2.39 mmol) in DMF (10 mL) and methanol (10 mL). Ozone was bubbled through the solution at room temperature for 20 minutes and the excess ozone was purged with a stream of nitrogen. Dimethyl sulfide (1.77 mL, 23.9 mmol) was added and the reaction was stirred at room temperature for 24 h. The solvent was evaporated and the resulting solid was dissolved in 20% MeOH-DCM. The crude product was added to a silica gel column and was eluted with 0-20% MeOH-DCM. The collected fractions gave the title compound (400 mg, 95% yield).

Provenance & Evidence