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

HRID 1672060Notes

Reaction equation

HRID 1672060 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4](O)[N:3]=1.O=P(Cl)(Cl)[Cl:12]>>[Cl:12][C:4]1[N:3]=[C:2]([CH3:1])[CH:7]=[C:6]([CH3:8])[N:5]=1

Participants

3

Reactant 2

HCID 95084,6-Dimethylpyrimidin-2-olHCID 24813Phosphorus oxychloride

Product 1

HCID 205502-Chloro-4,6-dimethylpyrimidine

Procedure

To a 50 ml single neck round-bottomed flask was added 4,6-dimethylpyrimidin-2-ol (5.0 g, 0.04 mol) followed by POCl3 (15.0 ml, 0.097 mol). The resulting suspension was heated to reflux overnight. Heating was stopped. After cooling, the mixture was concentrated, poured into crushed ice and extracted with diethyl ether (100 ml×2). The organic layer was washed with 10% NaHCO3 solution, dried over Na2SO4 and evaporated to get a pale yellow solid. Yield: 3.3 g (58%) 1H NMR (400 MHz, CDCl3): δ 2.48 (s, 6H), 6.97 (s, 1H). LCMS: (ES+) m/z=143.6 (M+H)+

Workup

  1. temperatureThe resulting suspension was heated
  2. temperatureto reflux overnight
  3. temperatureHeating
  4. temperatureAfter cooling
  5. concentrationthe mixture was concentrated
  6. additionpoured
  7. custominto crushed ice
  8. extractionextracted with diethyl ether (100 ml×2)
  9. washThe organic layer was washed with 10% NaHCO3 solution
  10. dry with materialdried over Na2SO4
  11. customevaporated
  12. customto get a pale yellow solid

Sources & evidence

ORD record
ord-3ee7c3cd2a7d43969d6b2f091874a539
Source dataset
uspto-grants-2011_08
Patent number
US07994171B2

Reaction notes

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