Phosphorus oxychloride → 4-Chloro-2,6-dimethylpyrimidine

HRID 2289541Notes

Reaction equation

HRID 2289541 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([CH3:8])[CH:5]=[C:4](O)[N:3]=1.P(Cl)(Cl)([Cl:12])=O>>[CH3:1][C:2]1[N:3]=[C:4]([Cl:12])[CH:5]=[C:6]([CH3:8])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178429343HCID 178429343, compound

Product 1

HCID 31541994-Chloro-2,6-dimethylpyrimidine

Procedure

2,4-Dimethyl-6-hydroxypyrimidine (20 g) was added to phosphorus oxychloride (120 ml) and the mixture was refluxed for 2 hours. Excess phosphorus oxychloride was removed in vacuo, water was added and the product was extracted into dichloromethane (2×200 ml), dried (Na2SO4) and the solvent removed to give 2,6-dimethyl-4-chloropyrimidine as an oil (21 g) which slowly crystallised on standing; NMR (CDCl3): 2.52 (s, 3H), 2.71 (s, 3H), 7.05 (s, 1H).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customExcess phosphorus oxychloride was removed in vacuo, water
  3. additionwas added
  4. extractionthe product was extracted into dichloromethane (2×200 ml)
  5. dry with materialdried (Na2SO4)
  6. customthe solvent removed

Sources & evidence

ORD record
ord-2eeb69b86ee547d895e6c64855e03937
Source dataset
uspto-grants-2000_07
Patent number
US06093718

Reaction notes

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