1,4-Dioxane--water (1/1) → HCID 57928026, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-2-[(E)-2-phenylethenyl]-5,8-dihydropyrido[2,3-d]pyrimidin-7(6H)-one (0.18 g, 0.64 mmol) was dissolved in a 2:1 solution of 1,4-dioxane/water (6 mL) and cooled to 0° C. NaIO4 (0.314 g, 1.47 mmol) and catalytic OsO4 (1 mL, 4% aq. solution) were added and the solution was then stirred at ambient temperature overnight. The reaction solution was concentrated under vacuum, diluted with water, and extracted with 10% MeOH/DCM (4×). The organic layers were combined, dried over Na2SO4, filtered and concentrated under vacuum. The crude residue was then purified by column chromatography (silica gel) using a DCM/DCM-MeOH—NH4OH (90:10:1) gradient to yield the desired compound (0.05 g, 44%).

Provenance & Evidence