Sodium Cyanide → 3-(4-cyano-5-ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 2270424Notes

Reaction equation

HRID 2270424 reaction equation
Br[C:2]1[C:7]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:6][C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1.[H-].[Na+].[C-:30]#[N:31].[Na+]>C(C1C=CC(C)=NC=1)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.[Cl-].[Zn+2].[Cl-]>[C:30]([C:2]1[C:7]([NH:8][S:9]([CH2:12][CH3:13])(=[O:11])=[O:10])=[CH:6][C:5]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:22])([F:23])[F:24])[N:16]([CH3:25])[C:15]2=[O:26])=[C:4]([F:27])[CH:3]=1)#[N:31]

Participants

7

Reactant 3

HCID 8929Sodium CyanideHCID 24758Sodium hydrideHCID 108744063-(4-bromo-5-ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione

Product 1

HCID 110910773-(4-cyano-5-ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedioneYield 61%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 3007855ZincchlorideCatalystHCID 77285-Ethyl-2-methylpyridineSolvent

Procedure

0.5 g (1.0 mmol) of 3-(4-bromo-5-ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione was dissolved in 10 ml of 5-ethyl-2-picoline, to which 0.04 g of sodium hydride was added under cooling with ice, and the mixture was stirred for 5 minutes. Next, 0.04 g of palladium acetate and 0.16 g of 1,4-bis(diphenylphosphino)ethane were added to the mixture, which was then stirred at 90° C. under an argon atmosphere for 1 hour. After the mixture was allowed to cool, 0.03 g of zinc chloride and 0.06 g of sodium cyanide were added to the mixture, which was then stirred for further 4 hours. After the reaction was completed, 61% of the title compound was detected as the relative area value in liquid chromatography.

Workup

  1. additionwas added
  2. temperatureunder cooling with ice
  3. stirringwas then stirred at 90° C. under an argon atmosphere for 1 hour
  4. temperatureto cool
  5. stirringwas then stirred for further 4 hours

Sources & evidence

ORD record
ord-56dd350c881546f7be1482cb9ad25335
Source dataset
uspto-grants-2001_12
Patent number
US06331628B1

Reaction notes

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