Dimethylformamide → HCID 21163078, compound

HRID 1278202Notes

Reaction equation

HRID 1278202 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][CH:15]=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1.P(Cl)(Cl)(Cl)=O.[OH-].[Na+].CN(C)[CH:25]=[O:26]>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[N:12]3[N:13]=[CH:14][C:15]([CH:25]=[O:26])=[C:11]3[N:10]=[CH:9][CH:8]=2)[CH:2]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 11206374HCID 11206374, compound

Product 1

HCID 21163078HCID 21163078, compound

Procedure

A 1.0 g. sample of 7-(3-pyridyl)pyrazolo[1,5-a]-pyrimidine is added to an ice cold solution of 1.0 ml. of phosphorus oxychloride in 3 ml. of N,N-dimethylformamide. The reaction mixture is heated on a steam bath for 3 hours and poured into ice. The mixture is made basic with a solution of sodium hydroxide and extracted into dichloromethane. The dichloromethane solution is washed with water 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.

Workup

  1. temperatureThe reaction mixture is heated on a steam bath for 3 hours
  2. additionpoured into ice
  3. extractionextracted into dichloromethane
  4. washThe dichloromethane solution is washed with water
  5. concentrationThe eluent is concentrated
  6. additiondiluted with hexane
  7. customto give the product of the example as crystals

Sources & evidence

ORD record
ord-3a359b6a09454a2d882ee0575e376313
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Reaction notes

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