Phenol → HCID 44216369, Verbindung

HRID 2217258Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2217258
[C:1]1([OH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[NH2:10][C:11]1[N:12]=[C:13]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[C:14]([C:18]2[CH:19]=[CH:20][C:21](=[O:27])[N:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=2)=[N:15][C:16]=1Br.CCOC(C)=O>CN1C(=O)CCC1.O>[NH2:10][C:11]1[N:12]=[C:13]([C:28]2[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=2)[C:14]([C:18]2[CH:19]=[CH:20][C:21](=[O:27])[N:22]([CH:24]([CH3:26])[CH3:25])[CH:23]=2)=[N:15][C:16]=1[O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Komponenten

7

Edukt 4

HCID 996PhenolHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 11429076HCID 11429076, Verbindung

Produkt 1

HCID 44216369HCID 44216369, VerbindungAusbeute 85,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of phenol (147 mg) in NMP (1.0 ml), was added 60% NaH (52 mg) under ice-bath cooling. After 5 minutes stirring, 5-(5-amino-6-bromo-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (100 mg) was added to the mixture at the same temperature. And then the mixture was heated at 100° C. with stirring for 5.5 hours. After cooling, EtOAc and water were poured into the mixture, and the organic layer was separated, washed with water and brine, and dried over MgSO4. The solvent was removed under reduced pressure. The residue was recrystallized from MeOH-IPE to give 5-(5-amino-6-phenoxy-3-phenyl-2-pyrazinyl)-1-isopropyl-2(1H)-pyridone (88 mg).

Aufarbeitung

  1. temperaturecooling
  2. stirringwith stirring for 5.5 hours
  3. temperatureAfter cooling
  4. customthe organic layer was separated
  5. washwashed with water and brine
  6. dry with materialdried over MgSO4
  7. customThe solvent was removed under reduced pressure
  8. customThe residue was recrystallized from MeOH-IPE

Quellen und Nachweise

ORD-Eintrag
ord-86186382428b4b699fb6ea99dcf83ebe
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407961B2

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