Water → 1-cyclobutyl-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

HRID 333755Notes

Reaction equation

HRID 333755 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.[CH:8]1([N:12]2[CH:17]=[C:16]([O:18]C)[C:15](=[O:20])[C:14]([C:21]3[N:25]([C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[N:24]=[CH:23][CH:22]=3)=[N:13]2)[CH2:11][CH2:10][CH2:9]1.O>C(#N)C>[CH:8]1([N:12]2[CH:17]=[C:16]([OH:18])[C:15](=[O:20])[C:14]([C:21]3[N:25]([C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[N:24]=[CH:23][CH:22]=3)=[N:13]2)[CH2:11][CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 680148321-cyclobutyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Product 1

HCID 895865101-cyclobutyl-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneYield 91.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of sodium iodide (2.11 g) in acetonitrile (84.3 mL) was added at room temperature chlorotrimethylsilane (1.78 mL) and the mixture was stirred for 30 min. Then, 1-cyclobutyl-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (0.91 g) was added, and the mixture was stirred at room temperature for 30 min, and further refluxed for 3 hr. The reaction mixture was allowed to cool to room temperature, water was added, and the mixture was stirred for 30 min, and extracted with ethyl acetate. The organic layer was washed with aqueous sodium thiosulfate solution and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was triturated with diisopropyl ether, and collected by filtration to give the title compound (800 mg).

Workup

  1. stirringthe mixture was stirred at room temperature for 30 min
  2. temperaturefurther refluxed for 3 hr
  3. stirringthe mixture was stirred for 30 min
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with aqueous sodium thiosulfate solution and saturated brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was triturated with diisopropyl ether
  9. filtrationcollected by filtration

Sources & evidence

ORD record
ord-b0afc3acb4f348759a36bb046ad48aeb
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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