1,4-Bis(diphenylphosphino)butane → 2-(3-Thienyl)-6-methyl-4-(1-methyl-3-trifluoromethyl-5-pyrazolyloxy)-pyrimidine

HRID 1288671Notes

Reaction equation

HRID 1288671 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[N:37]=[C:36]([O:38][C:39]2[N:43]([CH3:44])[N:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=2)[CH:35]=[C:34]([CH3:49])[N:33]=1.[S:50]1[CH:54]=[CH:53][C:52](B(O)O)=[CH:51]1.C(=O)([O-])O.[Na+]>C1C=CC(C#N)=CC=1.C1C=CC(C#N)=CC=1.Cl[Pd]Cl.O1CCOCC1.O.C1(C)C=CC=CC=1>[S:50]1[CH:54]=[CH:53][C:52]([C:32]2[N:37]=[C:36]([O:38][C:39]3[N:43]([CH3:44])[N:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=3)[CH:35]=[C:34]([CH3:49])[N:33]=2)=[CH:51]1

Participants

9

Reactant 4

HCID 821241,4-Bis(diphenylphosphino)butaneHCID 516892Sodium BicarbonateHCID 581760Thiophene-3-boronic acid2×HCID 537715222-Chloro-6-methyl-4-(1-methyl-3-trifluoromethyl-5-pyrazolyloxy)pyrimidine

Product 1

HCID 541263172-(3-Thienyl)-6-methyl-4-(1-methyl-3-trifluoromethyl-5-pyrazolyloxy)-pyrimidineYield 86%

Reagents, catalysts & solvents 4

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

Procedure

0.145 g of 1,4-bis(diphenylphosphino)butane and 0.115 g bis(benzonitrile)palladium(II)chloride are refluxed in 10 m toluene under nitrogen for 2 hours. At room temperature 1 g 2-chloro-6-methyl-4-(1-methyl-3-trifluoromethyl-5-pyrazolyloxy)pyrimidine, 0.55 g thiophene-3-boronic acid, 0.8 g sodium hydrogen carbonate, 15 mL water and 20 mL dioxane are added, and the mixture is heated to reflux. After 2 hours another 0.2 g thiophene-3-boronic acid are added, and reflux continued for 1 hour. The organic phase is washed with with water and chromatographed to give 1 g of the title compound (m.p. 122° C.).

Workup

  1. temperaturethe mixture is heated to reflux
  2. temperaturereflux
  3. washThe organic phase is washed with with water
  4. customchromatographed

Sources & evidence

ORD record
ord-11aca2d5d17a44df87dbc2409b9778c4
Source dataset
uspto-grants-1998_05
Patent number
US05747423

Reaction notes

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