HCID 11564642, Verbindung → 3-methyl-3H-imidazo[2,1-f][1,2,4]triazin-4-one

HRID 895109Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 895109
[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[N:9][CH:10]=[CH:11][N:5]2[N:4]=[C:3]1SC>C(O)C.[Ni]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]2=[N:9][CH:10]=[CH:11][N:5]2[N:4]=[CH:3]1

Komponenten

4

Edukt 1

HCID 11564642HCID 11564642, Verbindung

Produkt 1

HCID 116223593-methyl-3H-imidazo[2,1-f][1,2,4]triazin-4-oneAusbeute 24,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 935NickelKatalysatorHCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

3-Methyl-2-methylsulfanyl-3H-imidazo[2,1-f][1,2,4]triazin-4-one (0.81 g, 4.1 mmol) was suspended in ethanol (10 ml) and the mixture heated to 40° C. 6×1 ml pipette amounts of Raney-nickel (50 micron stored in water) were added in portions over 9 h. On complete addition the mixture was heated at 40° C. for a further 9 h. The mixture was allowed to cool to ambient temperature and the mixture filtered through Celite. The filtrate was evaporated and the residue purified by flash column chromatography on silica eluting with 2% methanol in dichloromethane. Collecting appropriate fractions gave 3-methyl-3H-imidazo[2,1-f][1,2,4]triazin-4-one (150 mg, 24%) as an off-white solid: δH (400 MHz, CDCl3) 3.59 (3H, s), 7.55 (1H, d, J1), 7.60 (1H, d, J1), 7.73 (1H, s).

Aufarbeitung

  1. additionOn complete addition the mixture
  2. temperaturewas heated at 40° C. for a further 9 h
  3. temperatureto cool to ambient temperature
  4. filtrationthe mixture filtered through Celite
  5. customThe filtrate was evaporated
  6. customthe residue purified by flash column chromatography on silica eluting with 2% methanol in dichloromethane
  7. customCollecting appropriate fractions

Quellen und Nachweise

ORD-Eintrag
ord-de3c9b362e134eb6b0725c439136ec3b
Quelldatensatz
uspto-grants-2005_07
Patentnummer
US06914060B2

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