1,4-Bis(diphenylphosphino)butane → 4-Methyl-2-methylthio-6-(4-trifluoromethylphenyl)-pyrimidine

HRID 427237Notes

Reaction equation

HRID 427237 reaction equation
C1(P(C2C=CC=CC=2)CCCCP(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.Cl[C:32]1[CH:37]=[C:36]([CH3:38])[N:35]=[C:34]([S:39][CH3:40])[N:33]=1.[F:41][C:42]([F:53])([F:52])[C:43]1[CH:48]=[CH:47][C:46](B(O)O)=[CH:45][CH:44]=1.C(=O)([O-])O.[Na+]>[Pd](Cl)Cl.C(#N)C1C=CC=CC=1.C(#N)C1C=CC=CC=1.O1CCOCC1.O.C1(C)C=CC=CC=1>[CH3:38][C:36]1[CH:37]=[C:32]([C:46]2[CH:47]=[CH:48][C:43]([C:42]([F:53])([F:52])[F:41])=[CH:44][CH:45]=2)[N:33]=[C:34]([S:39][CH3:40])[N:35]=1

Participants

9

Reactant 4

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 2411634-Chloro-6-methyl-2-(methylthio)pyrimidineHCID 516892Sodium BicarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acid

Product 1

HCID 183567874-Methyl-2-methylthio-6-(4-trifluoromethylphenyl)-pyrimidineYield 74.4%

Reagents, catalysts & solvents 4

HCID 498840Bis(benzonitrile)palladium chlorideCatalystHCID 962WaterSolventHCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Procedure

0.236 g of 1,4-bis(diphenylphosphino)butane and 0.20 g bis(benzonitrile)-palladium(II)chloride are refluxed in 10 m toluene under nitrogen for 2 hrs. At room temperature 0.95 g 4-chloro-6-methyl-2-methylthio-pyrimidine, 1.24 g 4-trifluoromethylphenyl boronic acid, 1.38 g sodium hydrogen carbonate, 30 ml water and 40 ml dioxane are added, and the mixture is heated to reflux for 5 hrs. The organic phase is washed with water and chromatographed to give 1.15 g of the title compound.

Workup

  1. temperaturethe mixture is heated
  2. temperatureto reflux for 5 hrs
  3. washThe organic phase is washed with water
  4. customchromatographed

Sources & evidence

ORD record
ord-5abaa105a24c441f839402e367d29832
Source dataset
uspto-grants-2001_11
Patent number
US06313072B1

Reaction notes

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