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4,6-Dimethylpyrimidin-2-ol → 2-Chloro-4,6-dimethylpyrimidine

HRID 230298
Notes
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Reaction equation

HRID 230298 reaction equation
P(Cl)(Cl)([Cl:3])=O.[CH3:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9](O)[N:8]=1.C(=O)([O-])O.[Na+]>O>[Cl:3][C:9]1[N:8]=[C:7]([CH3:6])[CH:12]=[C:11]([CH3:13])[N:10]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 95084,6-Dimethylpyrimidin-2-olHCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate

Product 1

HCID 205502-Chloro-4,6-dimethylpyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Under an argon atmosphere, phosphorus oxychloride (2 ml) was added to 4,6-dimethyl-2-hydroxypyrimidine (400 mg), and the resulting mixture was stirred for 1 hour while heating the mixture to reflux. The reaction solution was cooled to room temperature, and the cooled solution was added in small portions to water. After adding sodium hydrogen carbonate in small portions to the resulting mixture to neutralize it, the mixture was extracted with ethyl acetate. Organic layer was washed twice with water and once with saturated brine, and dried over anhydrous sodium sulfate. After removing anhydrous sodium sulfate by filtration, the filtrate was concentrated to obtain 2-chloro-4,6-dimethylpyrimidine (350 mg). (2) In the same manner as in Reference Example 8, 4-iodophenol (223 mg) and 2-chloro-4,6-dimethylpyrimidine (157 mg) were reacted by using sodium hydride to obtain 2-(4-iodophenoxy)-4,6-dimethylpyrimidine (226 mg).

Workup

  1. temperaturewhile heating the mixture
  2. temperatureto reflux
  3. extractionthe mixture was extracted with ethyl acetate
  4. washOrganic layer was washed twice with water and once with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removing anhydrous sodium sulfate
  7. filtrationby filtration
  8. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-5ccc550426494100875ec5a54fce51f6
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07566724B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes