Sodium Hydroxide → 6-(4-methoxy-2-methylphenyl)-5-methylpyrazin-2(1H)-one

HRID 2278828Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2278828
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=O)[C:10](=O)[CH3:11])=[C:5]([CH3:14])[CH:4]=1.C(O)(=O)C.[NH2:19][CH2:20][C:21]([NH2:23])=[O:22].[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:23][C:21](=[O:22])[CH:20]=[N:19][C:10]=2[CH3:11])=[C:5]([CH3:14])[CH:4]=1

Komponenten

5

Edukt 3

HCID 14798Sodium HydroxideHCID 203984852-Aminoacetamide acetateHCID 867178221-(4-Methoxy-2-methylphenyl)propane-1,2-dione

Produkt 1

HCID 867178236-(4-methoxy-2-methylphenyl)-5-methylpyrazin-2(1H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Reaktionsbedingungen

Temperatur
-10 °C

Versuchsvorschrift

C9 (4.0 g, 21 mmol) and glycinamide acetate (2.79 g, 20.8 mmol) were dissolved in methanol (40 mL) and cooled to −10° C. Aqueous sodium hydroxide solution (12 N, 3.5 mL, 42 mmol) was added, and the resulting mixture was slowly warmed to room temperature. After stirring for 3 days, the reaction mixture was concentrated in vacuo. The residue was diluted with water, and 1 N aqueous hydrochloric acid was added until the pH was approximately 7. The aqueous phase was extracted with ethyl acetate, and the combined organic extracts were washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The resulting residue was slurried with 3:1 ethyl acetate/heptane, stirred for 5 minutes, filtered, and concentrated in vacuo. Silica gel chromatography (Eluent: ethyl acetate) provided the product as a tan solid that contained 15% of an undesired regioisomer; this material was used without further purification. Yield: 2.0 g. LCMS m/z 231.1 [M+H+]. 1H NMR (400 MHz, CDCl3) δ 8.09 (s, 1H), 7.14 (d, J=8.2 Hz, 1H), 6.82-6.87 (m, 2H), 3.86 (s, 3H), 2.20 (s, 3H), 2.11 (s, 3H).

Aufarbeitung

  1. temperaturethe resulting mixture was slowly warmed to room temperature
  2. concentrationthe reaction mixture was concentrated in vacuo
  3. additionThe residue was diluted with water, and 1 N aqueous hydrochloric acid
  4. additionwas added until the pH was approximately 7
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic extracts were washed with saturated aqueous sodium chloride solution
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. stirringstirred for 5 minutes
  11. filtrationfiltered
  12. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-83e8faed9cff4880847176d667af78c4
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09133190B2

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