Methyl iodide → 5-Bromo-6-methoxy-2-methyl-3(2H)-pyridazinone

HRID 919307Notes

Reaction equation

HRID 919307 reaction equation
[Br:1][C:2]1[C:3](=[O:10])[NH:4][N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.[C:11]([O-])([O-])=O.[K+].[K+].CI>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([O:10][CH3:11])=[N:4][N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 901770424-Bromo-1,2-dihydro-1-methyl-3,6-pyridazinedione

Product 1

HCID 840759345-Bromo-6-methoxy-2-methyl-3(2H)-pyridazinoneYield 52.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution 4-bromo-1-methyl-1,2-dihydropyridazine-3,6-dione (216 mg, 1.05 mmol) in DMF (3.0 mL) was added K2CO3 (437 mg, 3.16 mmol), CH3I (299 mg, 2.11 mmol), the reaction mixture was stirred at 50° C. for 30 minutes. The mixture was cooled to ambient temperature, diluted with EtOAc (20 mL), washed with sodium bicarbonate (10 mL) and brine (10 mL), dried over MgSO4, filtered and concentrated. The residue was purified with silica gel column (Petroleum ether:ethyl acetate=4:1) to obtain product (120 mg, yield: 52.2%): LC/MS m/z=219.1 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. washwashed with sodium bicarbonate (10 mL) and brine (10 mL)
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified with silica gel column (Petroleum ether:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-f5b12e1a39904faf9f0ec21ac6243eae
Source dataset
uspto-grants-2016_03
Patent number
US09273033B2

Reaction notes

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