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

HRID 1278212Notes

Reaction equation

HRID 1278212 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 and 0.50 g. of cuprous cyanide in 25 ml. of N,N-dimethylformamide is heated at reflux temperature for 16 hours. The solvent is removed in vacuo and the residue is triturated with dichloromethane. The dichloromethane solution is passed through a column of hydrous magnesium silicate. The eluent is concentrated and hexane added to give the product of the example as tan crystals, m.p. 258°-260° C.

Workup

  1. additionA mixture of 1.0 g
  2. temperatureat reflux temperature for 16 hours
  3. customThe solvent is removed in vacuo
  4. customthe residue is triturated with dichloromethane
  5. concentrationThe eluent is concentrated
  6. additionhexane added
  7. customto give the product of the example as tan crystals, m.p. 258°-260° C.

Sources & evidence

ORD record
ord-fc8f06349240457799d107996b6f3c56
Source dataset
uspto-grants-1981_07
Patent number
US04281000

Reaction notes

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