Potassium Cyanide → 2-Chloro-6-methylpyrimidine-4-carbonitrile

HRID 962382Notes

Reaction equation

HRID 962382 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[C:4]([CH3:9])[N:3]=1.[C-:10]#[N:11].[K+]>CC#N>[Cl:1][C:2]1[N:7]=[C:6]([C:10]#[N:11])[CH:5]=[C:4]([CH3:9])[N:3]=1

Participants

4

Reactant 2

HCID 9032Potassium CyanideHCID 794712,4-Dichloro-6-methylpyrimidine

Product 1

HCID 123550822-Chloro-6-methylpyrimidine-4-carbonitrileYield 24.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

24.5 g of 2,4-dichloro-6-methylpyrimidine and 9.8 g of potassium cyanide were dissolved in 150 ml of CH3CN and refluxed for 8 days. The solvent was evaporated, the residue was dissolved in 150 ml of ethyl acetate and extracted twice with 50 ml H2O. The organic layer was dried over Na2SO4, the solvent was evaporated and the residue was purified on silica gel using a 4:1 mixture of benzene and methyl tert.butyl ether as eluent to give 5.2 g (24.8%) of 2-chloro-4-cyano-6-methyl pyrimidine of m.p. 57° C.

Workup

  1. temperaturerefluxed for 8 days
  2. customThe solvent was evaporated
  3. dissolutionthe residue was dissolved in 150 ml of ethyl acetate
  4. extractionextracted twice with 50 ml H2O
  5. dry with materialThe organic layer was dried over Na2SO4
  6. customthe solvent was evaporated
  7. customthe residue was purified on silica gel using
  8. additiona 4:1 mixture of benzene and methyl tert.butyl ether as eluent

Sources & evidence

ORD record
ord-8b0e0c5e2ef344649621ed9a43a25598
Source dataset
uspto-grants-1998_06
Patent number
US05759956

Reaction notes

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