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

HRID 2270423Notes

Reaction equation

HRID 2270423 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(C1C=C[C:35](C)=[N:36]C=1)C.[C-]#N.[Na+]>[Cu](Cl)Cl.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:35]([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:36]

Participants

7

Reactant 4

HCID 77285-Ethyl-2-methylpyridineHCID 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 79%

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

1.2 g (2.5 mmol) of 3-(4-bromo-5-ethylsulfonylamino-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)pyrimidinedione and 0.11 g of 55% sodium hydride in oil were added to 20 g of 5-ethyl-2-picoline and the mixture was stirred at room temperature for 30 minutes. Next, 0.07 g of copper(II) chloride and 0.15 g of sodium cyanide were added to the mixture, which was then stirred at 140° C. under an argon atmosphere for 1 hour. Further, 0.3 g of tetrakis(triphenylphosphine)palladium was added to the mixture, which was then heated with stirring for 3 hours. After the reaction was completed, 79% of the title compound was detected as the relative area value in liquid chromatography.

Workup

  1. stirringwas then stirred at 140° C. under an argon atmosphere for 1 hour
  2. temperaturewas then heated
  3. stirringwith stirring for 3 hours

Sources & evidence

ORD record
ord-f7c4ce6c50644725bd9d7572e33eaeea
Source dataset
uspto-grants-2001_12
Patent number
US06331628B1

Reaction notes

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