Water → 5-methyl-4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethyl-1H-1-pyrazolyl)pyrimidine

HRID 1180474Notes

Reaction equation

HRID 1180474 reaction equation
[CH3:1][C:2]1[C:3](S(C)(=O)=O)=[N:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[N:9]2)=[N:6][CH:7]=1.[F:21][C:22]([F:31])([F:30])[C:23]1[CH:24]=[C:25]([OH:29])[CH:26]=[CH:27][CH:28]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH3:1][C:2]1[C:3]([O:29][C:25]2[CH:26]=[CH:27][CH:28]=[C:23]([C:22]([F:21])([F:30])[F:31])[CH:24]=2)=[N:4][C:5]([N:8]2[CH:12]=[C:11]([C:13]([F:16])([F:15])[F:14])[CH:10]=[N:9]2)=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 73763-(Trifluoromethyl)phenolHCID 11430Potassium CarbonateHCID 121159885-methyl-4-methylsulfonyl-2-(4-trifluoromethyl-1H-1-pyrazolyl)pyrimidine

Product 1

HCID 115818495-methyl-4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethyl-1H-1-pyrazolyl)pyrimidineYield 72.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 11.2 g (36.4 mmol) of 5-methyl-4-methylsulfonyl-2-(4-trifluoromethyl-1H -1-pyrazolyl)pyrimidine, 7.7 g (47.4 mmol) of 3-trifluoromethylphenol and 10.1 g (72.9 mmol) of K2CO3 in 200 ml of DMF is stirred at RT for 24 h. It is then poured into 200 ml of water and extracted with four times 100 ml of CH2Cl2. The combined organic phase is dried over Na2SO4, filtered and concentrated. Chromatographic purification on silica gel with heptane/ethyl acetate (1:1) as eluent gives 10.2 g (72%) of 5-methyl-4-(3-trifluoromethylphenoxy)-2-(4-trifluoromethyl-1H-1-pyrazolyl)pyrimidine as colourless crystals having a melting point of 103-105° C.

Workup

  1. extractionextracted with four times 100 ml of CH2Cl2
  2. dry with materialThe combined organic phase is dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customChromatographic purification on silica gel with heptane/ethyl acetate (1:1) as eluent

Sources & evidence

ORD record
ord-0e512b70f3d5446bac0a6379e65886bc
Source dataset
uspto-grants-2007_10
Patent number
US07282469B2

Reaction notes

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