Phosphorus oxychloride → 7-(3-Pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

HRID 1278213Notes

Reaction equation

HRID 1278213 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]([NH2:18])=O)=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1.P(Cl)(Cl)(Cl)=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][C:15]([C:16]#[N:18])=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 145018627-(Pyridin-3-yl)pyrazolo[1,5-a]pyrimidine-3-carboxamide

Product 1

HCID 112183037-(3-Pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile

Procedure

A mixture of 1.0 g. of 7-(3-pyridyl)pyrazolo[1,5-a]-pyrimidine-3-carboxamide and 5 ml. of phosphorus oxychloride is heated at reflux temperature for 3 hours. The mixture is concentrated to dryness in vacuo. The residue is dissolved in dichloromethane and washed with a saturated solution of sodium bicarbonate. The dichloromethane solution is dried over magnesium sulfate and passed through a column of hydrous magnesium silicate. The eluent is concentrated and diluted with hexane to give the product of the example as crystals, m.p. 258°-260° C.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureat reflux temperature for 3 hours
  3. concentrationThe mixture is concentrated to dryness in vacuo
  4. dissolutionThe residue is dissolved in dichloromethane
  5. washwashed with a saturated solution of sodium bicarbonate
  6. dry with materialThe dichloromethane solution is dried over magnesium sulfate
  7. concentrationThe eluent is concentrated
  8. additiondiluted with hexane
  9. customto give the product of the example as crystals, m.p. 258°-260° C.

Sources & evidence

ORD record
ord-c0837f9056ba4ae48eea93e8ce96ecf2
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Reaction notes

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