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

HRID 1278234Notes

Reaction equation

HRID 1278234 reaction equation
Br[C:2]1[CH:3]=[N:4][N:5]2[C:10]([C:11]3[CH:12]=[N:13][CH:14]=[CH:15][CH:16]=3)=[CH:9][CH:8]=[N:7][C:6]=12.[CH3:17][N:18](C)C=O>>[N:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:10]2[N:5]3[N:4]=[CH:3][C:2]([C:17]#[N:18])=[C:6]3[N:7]=[CH:8][CH:9]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 12766251HCID 12766251, compound

Product 1

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

Procedure

A mixture of 1.0 g. of 3-bromo-7-(3-pyridyl)pyrazolo[1,5-a]pyrimidine, 0.45 g. of cuprous cyanide and 25 ml. of N,N-dimethylformamide is refluxed for 16 hours. The solvent is removed and the residue triturated with dichloromethane. The dichloromethane extract is passed through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give the product of the example, m.p. 258°-260° C.

Workup

  1. additionA mixture of 1.0 g
  2. customThe solvent is removed
  3. customthe residue triturated with dichloromethane
  4. extractionThe dichloromethane extract
  5. concentrationThe eluent is concentrated
  6. additionhexane added
  7. customto give the product of the example, m.p. 258°-260° C.

Sources & evidence

ORD record
ord-09c3c5f4a920417284136cbfc11f6759
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Reaction notes

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