Dimethylformamide → 4-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile

HRID 1447877Notes

Reaction equation

HRID 1447877 reaction equation
Br[C:2]1[N:3]=[CH:4][N:5]2[C:10]([C:11]3[CH:12]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:14]=[CH:15][CH:16]=3)=[CH:9][CH:8]=[N:7][C:6]=12.[CH3:21][N:22](C)C=O>>[F:18][C:17]([F:20])([F:19])[C:13]1[CH:14]=[CH:15][CH:16]=[C:11]([C:10]2[N:5]3[CH:4]=[N:3][C:2]([C:21]#[N:22])=[C:6]3[N:7]=[CH:8][CH:9]=2)[CH:12]=1

Participants

3

Reactant 2

HCID 6228DimethylformamideHCID 233298344-(alpha,alpha,alpha-Trifluoro-m-tolyl)-8-bromoimidazo[1,5-a]pyrimidine

Product 1

HCID 157125564-(alpha,alpha,alpha-Trifluoro-m-tolyl)imidazo[1,5-a]pyrimidine-8-carbonitrile

Procedure

A mixture of 1.0 g. of 8-bromo-4-(α,α,α-trifluoro-m-tolyl)imidazo[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 under reduced pressure. The residue is extracted with methylene chloride and the solution passed through a column of hydrous magnesium silicate. The eluent is collected, concentrated and n-hexane added while heating. The product separates as crystals, m.p. 168°-169° C.

Workup

  1. additionA mixture of 1.0 g
  2. customThe solvent is removed under reduced pressure
  3. extractionThe residue is extracted with methylene chloride
  4. customThe eluent is collected
  5. concentrationconcentrated
  6. additionn-hexane added
  7. temperaturewhile heating

Sources & evidence

ORD record
ord-cd4d1a0003d14b8d90a8bbe20d05dfd1
Source dataset
uspto-grants-1979_12
Patent number
US04178449

Reaction notes

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