Phosphorus oxychloride → 5,7-Dichloro-[1,2,4]triazolo[1,5-c]pyrimidine

HRID 2171504Notes

Reaction equation

HRID 2171504 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](O)[N:5]2[N: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[N:9]=[CH:10][N:11]=[C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178517804HCID 178517804, compound

Product 1

HCID 552791785,7-Dichloro-[1,2,4]triazolo[1,5-c]pyrimidine

Conditions

Temperature
120 °C

Procedure

927 mg (4.19 mmol) of 7-chloro[1,2,4]triazolo[1,5-c]pyrimidin-5-ol (Example 52A) are suspended in 16.9 g (110.13 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. 389 mg (49% of theory) of the product are obtained.

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. custom389 mg (49% of theory) of the product are obtained

Sources & evidence

ORD record
ord-7c4deaedff754371a737dcd26660582c
Source dataset
uspto-grants-2015_06
Patent number
US09051323B2

Reaction notes

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