1,4-Dioxane → HCID 178519955, compound

Participants

Reaction Steps

To a suspension of 2-[(E)-2-phenylethenyl]-1H-pyrimido[5,4-b][1,4]oxazin-7(6H)-one (106 mg, 0.418 mmol) in 1,4-dioxane (12 mL) and water (3 mL) was added NaIO4 (357 mg, 1.67 mmol) and OsO4 (00.1 mL, 4% wt in water) and the reaction mixture was stirred at room temperature. After 2 h, and additional 3 mL of 1,4-dioxane and 180 mg of NaIO4 were added. After a total of 7.5 h, the reaction was capped and stored in a freezer for the weekend. After warming to room temperature, additional OsO4 (0.1 mL, 4% wt in water) was added and the reaction was stirred for an additional 4 h. The solvent was evaporated to give a white solid which was dissolved in DCM and water. The aqueous layer was extracted with 10% MeOH-DCM (6×). The combined organic extracts were dried over Na2SO4, filtered, and concentrated to give a light tan solid (92 mg) which was not purified further.

Provenance & Evidence