1,4-Dioxane--water (1/1) → HCID 86635373, compound

Participants

Reaction Conditions

Reaction Steps

To 4-chloro-2-[(E)-2-phenylethenyl]-6,7-dihydro-5H-pyrano[2,3-d]pyrimidine (0.21 g, 0.79 mmol) was dissolved in a 2:1 solution of 1,4-dioxane/water (6 mL) and cooled to 0° C. NaIO4 (0.50 g, 2.4 mmol) and catalytic OsO4 (0.25 mL, 4% aq. solution) were added and the solution was then stirred at ambient temperature for 2 h. The reaction solution was diluted with water (10 mL) and extracted with EtOAc (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-MeOH (90:10) to yield the desired compound as an off-white solid (0.055 g, 36%).

Provenance & Evidence