Pyrazole → 2-(1H-Pyrazol-1-yl)pyrimidine

HRID 1038120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1038120
[NH:1]1[CH:5]=[CH:4][CH:3]=[N:2]1.Br[C:7]1[N:12]=[CH:11][CH:10]=[CH:9][N:8]=1.N1C2C(=CC=C3C=2N=CC=C3)C=CC=1.C(OCC)(=O)C>CC(N(C)C)=O.[Cu]I.O>[N:1]1([C:7]2[N:12]=[CH:11][CH:10]=[CH:9][N:8]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Komponenten

8

Edukt 4

HCID 1048PyrazoleHCID 13181,10-PhenanthrolineHCID 8857Ethyl AcetateHCID 783452-Bromopyrimidine

Produkt 1

HCID 111707712-(1H-Pyrazol-1-yl)pyrimidineAusbeute 15,7 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 962WaterLösungsmittelHCID 31374DimethylacetamideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A reaction mixture containing pyrazole (2 g, 29 mmol), 2-bromopyrimidine (3.8 g, 24 mmol), copper (I) iodide (0.91 g, 4.8 mmol) and 1,10-phenanthroline (1.7 g, 9.6 mmol) in DMA was heated at 140° C. in a sealed tube for 6 hours. After the reaction, ethyl acetate (30 mL) was added, followed by water. The aqueous layer was extract three times (20 mL) and the organic layer was collected, dry over sodium sulfate. After concentration under vacuum, the crude product was purified using column chromatography (10% ethyl acetate in dichloromethane) to give 0.55 g of pure product. 15% yield. MS (ESMS, M+H 146).

Aufarbeitung

  1. additionwas added
  2. extractionThe aqueous layer was extract three times (20 mL)
  3. customthe organic layer was collected
  4. dry with materialdry over sodium sulfate
  5. concentrationAfter concentration under vacuum
  6. customthe crude product was purified

Quellen und Nachweise

ORD-Eintrag
ord-def692fd8412499c9e784ff4a9993002
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08546404B2

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