Ammonium formate → 2,5-Dimethyl-3-piperazin-1-ylpyrazine

HRID 1727179Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1727179
[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][N:11](CC3C=CC=CC=3)[CH2:10][CH2:9]2)=[N:6][C:5]([CH3:21])=[CH:4][N:3]=1.C([O-])=O.[NH4+]>CO.[Pd]>[CH3:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[N:6][C:5]([CH3:21])=[CH:4][N:3]=1

Komponenten

5

Edukt 2

HCID 2723923Ammonium formate2×HCID 690591832,5-Dimethyl-3-[4-(phenylmethyl)piperazin-1-yl]pyrazine

Produkt 1

HCID 38119102,5-Dimethyl-3-piperazin-1-ylpyrazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysator2×HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of 2,5-dimethyl-3-[4-(phenylmethyl)piperazin-1-yl]pyrazine (Preparation 17, 1.14 g, 4.04 mmol) in methanol (80 ml) was added ammonium formate (1.27 g, 20.2 mmol) followed by palladium (10% w/w on carbon, 0.17 g) under a nitrogen atmosphere. The reaction mixture was heated under reflux, after 2.5 h, more ammonium formate (0.64 g, 10.1 mmol) and palladium (0.06 g) were added. The reaction mixture was filtered through Celite® washed with methanol and concentrated in vacuo. The crude product was purified by flash chromatography using silica gel eluting with methanol:dichloromethane (8:92 and then 10:90) and then methanol:dichloromethane:0.88 ammonia solution (10:90:1). The title compound was obtained as a white solid (0.35 g, 45%).

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureunder reflux, after 2.5 h
  3. filtrationThe reaction mixture was filtered through Celite®
  4. washwashed with methanol
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ffd35b0a8650436092c687bfa2f79250
Quelldatensatz
uspto-grants-2009_02
Patentnummer
US07494992B2

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