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

HRID 333731Notes

Reaction equation

HRID 333731 reaction equation
[I-].[Na+].Cl[Si](C)(C)C.[CH:8]1([CH2:11][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)[CH2:10][CH2:9]1.O>C(#N)C>[CH:8]1([CH2:11][N:12]2[CH:17]=[C:16]([OH:18])[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)[CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 962WaterHCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 680148501-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one

Product 1

HCID 895865391-(cyclopropylmethyl)-5-hydroxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-oneYield 79.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of sodium iodide (3.75 g) in acetonitrile (150 mL) was added chlorotrimethylsilane (3.17 mL) with stirring at room temperature for 30 min. Then, 1-(cyclopropylmethyl)-5-methoxy-3-(1-phenyl-1H-pyrazol-5-yl)pyridazin-4(1H)-one (1.613 g) was added, and the mixture was stirred for 30 min at the same temperature and further refluxed for 4 hr. The reaction mixture was allowed to cool to room temperature, poured into water and the mixture was stirred for 30 min. The mixture was extracted with ethyl acetate, and the organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The obtained residue was triturated with diisopropyl ether, collected by filtration, washed successively with ethyl acetate and diisopropyl ether, and dried to give the title compound (1.23 g) as a pale-brown solid.

Workup

  1. stirringthe mixture was stirred for 30 min at the same temperature
  2. temperaturefurther refluxed for 4 hr
  3. temperatureto cool to room temperature
  4. stirringthe mixture was stirred for 30 min
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe organic layer was washed with saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe obtained residue was triturated with diisopropyl ether
  10. filtrationcollected by filtration
  11. washwashed successively with ethyl acetate and diisopropyl ether
  12. customdried

Sources & evidence

ORD record
ord-8282ed1d7daf40b9b21ba2dcba3dcbbb
Source dataset
uspto-grants-2014_11
Patent number
US08883788B2

Reaction notes

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