Methyl iodide → 5-Bromo-6-methoxy-2-methylpyridazin-3(2H)-one

HRID 919307Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 919307
[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

Komponenten

6

Edukt 3

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

Produkt 1

HCID 840759345-Bromo-6-methoxy-2-methylpyridazin-3(2H)-oneAusbeute 52,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

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)+.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f5b12e1a39904faf9f0ec21ac6243eae
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09273033B2

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