1,4-Dioxane → HCID 178519955, compound

HRID 657167Notes

Reaction equation

HRID 657167 reaction equation
C1(/C=[CH:8]/[C:9]2[NH:18][C:17]3[C:12]([O:13][CH2:14][C:15](=[O:19])[N:16]=3)=[CH:11][N:10]=2)C=CC=CC=1.[O:20]1CCOCC1>O.C(Cl)Cl.O=[Os](=O)(=O)=O>[O:19]=[C:15]1[CH2:14][O:13][C:12]2=[CH:11][N:10]=[C:9]([CH:8]=[O:20])[NH:18][C:17]2=[N:16]1

Participants

6

Reactant 2

HCID 312751,4-Dioxane2×HCID 178516869HCID 178516869, compound

Product 1

HCID 178519955HCID 178519955, compound

Reagents, catalysts & solvents 3

HCID 30318Osmium TetroxideCatalyst2×HCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

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.

Workup

  1. customAfter a total of 7.5 h, the reaction was capped
  2. temperatureAfter warming to room temperature
  3. stirringthe reaction was stirred for an additional 4 h
  4. customThe solvent was evaporated
  5. customto give a white solid which
  6. extractionThe aqueous layer was extracted with 10% MeOH-DCM (6×)
  7. dry with materialThe combined organic extracts were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-6c334e8a726a46ea99c9221a8883f70c
Source dataset
uspto-grants-2011_12
Patent number
US08071592B2

Reaction notes

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