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

HRID 895109Notes

Reaction equation

HRID 895109 reaction equation
[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

Participants

4

Reactant 1

HCID 11564642HCID 11564642, compound

Product 1

HCID 116223593-methyl-3H-imidazo[2,1-f][1,2,4]triazin-4-oneYield 24.4%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-de3c9b362e134eb6b0725c439136ec3b
Source dataset
uspto-grants-2005_07
Patent number
US06914060B2

Reaction notes

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