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

HRID 1910807Notes

Reaction equation

HRID 1910807 reaction equation
Cl.[CH3:2][C:3]1[CH:8]=[C:7]([CH3:9])[NH:6][C:5](=O)[N:4]=1.O=P(Cl)(Cl)[Cl:13]>>[Cl:13][C:5]1[N:4]=[C:3]([CH3:2])[CH:8]=[C:7]([CH3:9])[N:6]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 123431664,6-Dimethyl-2(1H)-pyrimidinone hydrochloride

Product 1

HCID 205502-Chloro-4,6-dimethylpyrimidineYield 56.1%

Procedure

A suspension of 4,6-dimethyl-1H-pyrimidin-2-one hydrochloride (3.0 g, 18.75 mmol) in dry POCl3 (25 mL, 272 mmol) was refluxed for 18 hours. The reaction mixture was evaporated to dryness and the residue dissolved in dichloromethane. The solution was washed with sodium bicarbonate solution until the pH of the aqueous washings were neutral, then with brine, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to afford 2-chloro-4,6-dimethyl-pyrimidine (1.5 g, 56%) as a solid.

Workup

  1. temperaturewas refluxed for 18 hours
  2. customThe reaction mixture was evaporated to dryness
  3. dissolutionthe residue dissolved in dichloromethane
  4. washThe solution was washed with sodium bicarbonate solution until the pH of the aqueous washings
  5. dry with materialwith brine, dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-7653f81e76fb4780ad016929ecb9e0e0
Source dataset
uspto-grants-2013_12
Patent number
US08604029B2

Reaction notes

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