4-Aminopyridine → HCID 66893771, Verbindung

HRID 1174587Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1174587
[N:1]1[CH:6]=[CH:5][C:4]([NH2:7])=[CH:3][CH:2]=1.[CH3:8][S:9][C:10](SC)=[CH:11][C:12]#[N:13].[H-].[Na+]>CN(C=O)C>[CH3:8][S:9][C:10]([NH:7][C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1)=[CH:11][C:12]#[N:13]

Komponenten

5

Edukt 3

HCID 17274-AminopyridineHCID 24758Sodium hydrideHCID 53254452-Propenenitrile, 3,3-bis(methylthio)-

Produkt 1

HCID 66893771HCID 66893771, VerbindungAusbeute 90,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of pyridin-4-ylamine (1.0 g, 11.0 mmol) and 3,3-Bis-methylsulfanyl-acrylonitrile (2.05 g, 12.6 mmol) in DMF at room temperature, was added powdered 4 A molecular sieves. The mixture was stirred for 1 hr. Subsequently the mixture was cooled to 0° C., 60% NaH dispersion in oil (0.92 g, 23.0 mmol) was added portionwise over 1 hr. and it was stirred at 0° C. for an additional 2 hrs. The cold bath was removed and the mixture was stirred at room temperature for 20 hrs. DMF was removed in vacuo and the crude was purified by column chromatography (gradient of EtOAc to 25% MeOH/EtOAc) to afford the desired product as an off-white solid (1.9 g, 89%).

Aufarbeitung

  1. stirringand it was stirred at 0° C. for an additional 2 hrs
  2. customThe cold bath was removed
  3. stirringthe mixture was stirred at room temperature for 20 hrs
  4. customDMF was removed in vacuo
  5. customthe crude was purified by column chromatography (gradient of EtOAc to 25% MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-17a558ce781645dfb4399ecda90d8718
Quelldatensatz
uspto-grants-2010_11
Patentnummer
US07838520B2

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