Ethanol → 5-(2-Methylsulfanylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

HRID 394474Notes

Reaction equation

HRID 394474 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH:9]([C:14](=O)[C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=2)[CH2:10][C:11](O)=[O:12])[CH:6]=[CH:5][N:4]=1.C(O)C.[NH2:29][NH2:30].C(OCC)(=O)C>CCOCC>[CH3:1][S:2][C:3]1[N:8]=[C:7]([CH:9]2[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[CH:16]=3)=[N:30][NH:29][C:11](=[O:12])[CH2:10]2)[CH:6]=[CH:5][N:4]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8857Ethyl AcetateHCID 9321HydrazineHCID 181766313-(2-Methylsulfanylpyrimidin-4-yl)-4-oxo-4-(3-trifluoromethylphenyl)butyric Acid

Product 1

HCID 181766265-(2-Methylsulfanylpyrimidin-4-yl)-6-(3-trifluoromethylphenyl)-4,5-dihydro-2H-pyridazin-3-one

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Compound 5 (6.58 g, 17.8 mmol), and ethanol (200 mL) were combined under argon. Hydrazine (835 μL, 26.6 mmol) was added and the resulting solution was heated at reflux for 4 h. The solution was cooled and rotary evaporated. Ethyl acetate was added followed by the addition of ether. The solution was again rotary evaporated to afford a foam (6) which was used as is for the synthesis of 7.

Workup

  1. temperaturethe resulting solution was heated
  2. temperatureat reflux for 4 h
  3. temperatureThe solution was cooled
  4. customThe solution was again rotary evaporated

Sources & evidence

ORD record
ord-b1dc4c7249894badb5d7628b6661dcce
Source dataset
uspto-grants-2003_08
Patent number
US06602872B1

Reaction notes

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