Water → HCID 86600671, compound

HRID 970275Notes

Reaction equation

HRID 970275 reaction equation
[CH3:1][C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([N:9]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[N:10]2)[CH:3]=1.[OH:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:27])[F:26])[CH:20]=1.C([O-])([O-])=O.[K+].[K+].O>C(#N)C>[CH3:1][C:2]1[N:7]=[C:6]([O:18][C:19]2[CH:24]=[CH:23][N:22]=[C:21]([C:25]([F:28])([F:26])[F:27])[CH:20]=2)[N:5]=[C:4]([N:9]2[CH:13]=[C:12]([C:14]([F:17])([F:16])[F:15])[CH:11]=[N:10]2)[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 64179120HCID 64179120, compoundHCID 178516505HCID 178516505, compound

Product 1

HCID 86600671HCID 86600671, compoundYield 85.6%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 0.63 g (2.4 mmol) of 6-methyl-4-(4-trifluoromethyl-1H-1-pyrazolyl)-2-chloropyrimidine, 0.39 g (2.4 mmol) of 4-hydroxy-2-trifluoromethylpyridine and 0.66 g (4.8 mmol) of K2CO3 in 20 ml of acetonitrile stirred under reflux for 8 h and then allowed to stand at RT overnight. The mixture is poured 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 (7:3) gives 0.8 g (85%) of 6-methyl-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-8fb6d895406946f4910c38f2bb8c1c89
Source dataset
uspto-grants-2007_12
Patent number
US07312180B2

Reaction notes

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