Methyl morpholine oxide → HCID 58001767, compound

To a white suspension of 3-chloro-6-ethenyl-4-methylpyridazine (34.1 mg, 0.221 mmol), NaIO4 (189 mg, 0.882 mmol), 4-methylmorpholine N-oxide (28.4 mg, 0.243 mmol) in CH3CN (3 mL) and water (1.5 mL) was added OsO4 (0.013 mL, 2.206 μmol), and the mixture was stirred at room temperature for 3 days. The reaction was monitored by LCMS and starting material was observed. The reaction mixture was heated at 60° C. overnight and no more starting material was observed. Solvents were evaporated in vacuo and the residue was partitioned between EtOAc and water. The aqueous layer was extracted with additional EtOAc. The combined organic phases were washed with water, dried with over anhydrous MgSO4, filtered and concentrated under reduced pressure to give 31.1 mg of the title compound as a white solid. It will be used in the next step without prior purification.

1. temperatureThe reaction mixture was heated at 60° C. overnight
2. customSolvents were evaporated in vacuo
3. customthe residue was partitioned between EtOAc and water
4. extractionThe aqueous layer was extracted with additional EtOAc
5. washThe combined organic phases were washed with water
6. dry with materialdried with over anhydrous MgSO4
7. filtrationfiltered
8. concentrationconcentrated under reduced pressure

ORD record

ord-5079678b46c741edb9054e87bf9266c8

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08097628B2