Dimethylformamide → 7-(3-Pyridyl)pyrazolo[1,5-a]pyrimidine-3-carbonitrile
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]=1Participants
3
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
- additionA mixture of 1.0 g
- temperatureat reflux temperature for 16 hours
- customThe solvent is removed in vacuo
- customthe residue is triturated with dichloromethane