Water → HCID 86600670, compound

HRID 970274Notes

Reaction equation

HRID 970274 reaction equation
[CH2:1]([C:3]1[N:8]=[C:7](S(C)(=O)=O)[N:6]=[C:5]([N:13]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[N:14]2)[CH:4]=1)[CH3:2].[OH:22][C:23]1[CH:28]=[CH:27][N:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH2:1]([C:3]1[N:8]=[C:7]([O:22][C:23]2[CH:28]=[CH:27][N:26]=[C:25]([C:29]([F:32])([F:30])[F:31])[CH:24]=2)[N:6]=[C:5]([N:13]2[CH:17]=[C:16]([C:18]([F:21])([F:20])[F:19])[CH:15]=[N:14]2)[CH:4]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 69421948HCID 69421948, compoundHCID 178516505HCID 178516505, compound

Product 1

HCID 86600670HCID 86600670, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.4 g (1.25 mmol) of 6-ethyl-4-(4-trifluoromethyl-1H-1-pyrazolyl)-2-methylsulfonylpyrimidine, 0.2 g (1.25 mmol) of 4-hydroxy-2-trifluoromethylpyridine and 0.345 g (2.5 mmol) of K2CO3 in 20 ml of acetonitrile is stirred under reflux for 8 h and then allowed to stand at RT overnight. The mixture is put into 40 ml of water and extracted four times with in each case 20 ml of CH2Cl2. The combined organic phases are dried over Na2SO4 and concentrated. Chromatographic purification on silica gel using heptane/ethyl acetate (1:1) gives 0.33 g (65%) of 6-ethyl-4-(4-trifluoromethyl-1H-1-pyrazolyl)-2-(2-trifluoromethylpyridin-4-yloxy)pyrimidine.

Workup

  1. temperatureunder reflux for 8 h
  2. extractionextracted four times with in each case 20 ml of CH2Cl2
  3. dry with materialThe combined organic phases are dried over Na2SO4
  4. concentrationconcentrated
  5. customChromatographic purification on silica gel

Sources & evidence

ORD record
ord-8d8c30b678a1424bb4e9e7129a1b702a
Source dataset
uspto-grants-2007_12
Patent number
US07312180B2

Reaction notes

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