Phosphorus oxychloride → 5,7-Dichloroimidazo[1,2-c]pyrimidine

HRID 2171481Notes

Reaction equation

HRID 2171481 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](O)[N:5]2[CH:9]=[CH:10][N:11]=[C:4]2[CH:3]=1.P(Cl)(Cl)([Cl:14])=O>>[Cl:14][C:6]1[N:5]2[CH:9]=[CH:10][N:11]=[C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517803HCID 178517803, compound

Product 1

HCID 469421175,7-Dichloroimidazo[1,2-c]pyrimidine

Conditions

Temperature
120 °C

Procedure

38.3 g (225.86 mmol) of 7-chloroimidazo[1,2-c]pyrimidin-5-ol are suspended in 450.2 g (2936 mmol) of phosphoryl chloride under argon and heated at 120° C. for 4 h. After this time, the excess phosphoryl chloride is removed in vacuo, and the residue is distilled together with toluene. The residue is suspended in water, the pH is brought to 7 with saturated aqueous sodium bicarbonate solution, and the precipitated solid is filtered off with suction. The latter is washed with water and dried over phosphorus pentoxide for 18 h. 33.5 g (67% of theory) of the product are obtained as a solid.

Workup

  1. customAfter this time, the excess phosphoryl chloride is removed in vacuo
  2. distillationthe residue is distilled together with toluene
  3. filtrationthe precipitated solid is filtered off with suction
  4. washThe latter is washed with water
  5. dry with materialdried over phosphorus pentoxide for 18 h
  6. custom33.5 g (67% of theory) of the product are obtained as a solid

Sources & evidence

ORD record
ord-ed8590d4b92b42138a2e6d52342294e4
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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