Methyl iodide → Ethyl 1-methyl-6-oxo-1,6-dihydropyridazine-4-carboxylate

HRID 2243893Notes

Reaction equation

HRID 2243893 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][NH:9][C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2].[C:13](=O)([O-])[O-].[K+].[K+].CI.C(OCC)(=O)C>CN(C=O)C.O>[CH2:1]([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]([CH3:13])[C:10](=[O:12])[CH:11]=1)=[O:5])[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 12376258Ethyl 6-oxo-1,6-dihydropyridazine-4-carboxylate

Product 1

HCID 59006703Ethyl 1-methyl-6-oxo-1,6-dihydropyridazine-4-carboxylateYield 66.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of 6-oxo-1,6-dihydro-pyridazine-4-carboxylic acid ethyl ester (1.0 g, 5.9 mmol) in anhydrous DMF (15 mL) was added potassium carbonate (3.29 g, 23.8 mmol). The reaction mixture was cooled to 0° C. and methyl iodide (1.0 mL, 16 mmol) was added dropwise. The reaction mixture was allowed to reach room temperature and was then heated at 60° C. for 15 minutes. The reaction was cooled to below 0° C. and ethyl acetate and water were added. The organic layer was separated, washed with cold water and brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by RP-HPLC using a linear gradient of acetonitrile in 0.1 M ammonium acetate buffer to afford the title compound (712 mg, 66%).

Workup

  1. customto reach room temperature
  2. temperaturewas then heated at 60° C. for 15 minutes
  3. temperatureThe reaction was cooled to below 0° C.
  4. customThe organic layer was separated
  5. washwashed with cold water and brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated
  8. customThe residue was purified by RP-HPLC

Sources & evidence

ORD record
ord-11b4e6a2b91744eba563880f49a24a0f
Source dataset
uspto-grants-2010_03
Patent number
US07678796B2

Reaction notes

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