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

HRID 1282157Notes

Reaction equation

HRID 1282157 reaction equation
O[C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1.[OH-].[Na+].P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

4

Reactant 3

HCID 95084,6-Dimethylpyrimidin-2-olHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychloride

Product 1

HCID 205502-Chloro-4,6-dimethylpyrimidine

Procedure

A solution of 2-hydroxy-4,6-dimethylpyrimidine (5.0 g) in phosphorous oxychloride (19 ml) was refluxed under heating for 9 hr. The reaction mixture was added dropwise to an aqueous sodium hydroxide solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated to give a yellow oil (3.0 g). The obtained yellow oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=30:1) to give the title compound (2.4 g) as a pale-yellow oil.

Workup

  1. temperatureunder heating for 9 hr
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-e3c81533846240b1b6bea0e02bc20ace
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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