p-Fluoronitrobenzene → 4,6-Dimethyl-2-(4-nitrophenyl)pyrimidine

HRID 477393Notes

Reaction equation

HRID 477393 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4](S)[N:3]=1.F[C:11]1[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([C:11]2[CH:16]=[CH:15][C:14]([N+:17]([O-:19])=[O:18])=[CH:13][CH:12]=2)[N:3]=1

Participants

5

Reactant 3

HCID 9590p-FluoronitrobenzeneHCID 11430Potassium CarbonateHCID 1784266324,6-dimethylpyrimidine-2-thiol

Product 1

HCID 4591324,6-Dimethyl-2-(4-nitrophenyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 25.0 grams (g) 4,6-dimethyl-2-mercaptopyrimidine, 25.1 g 4-fluoronitrobenzene and 24.6 g potassium carbonate in 750 milliliters (ml) acetonitrile was refluxed for 16 hours. The solution was then filtered hot through a pad of dicalite. The dicalite was washed with 300 ml hot acetonitrile. The solvent was evaporated from the combined filtrates giving a waxy yellow solid. This solid was triturated with hexanes giving 42.5 g yellow solid.

Workup

  1. filtrationThe solution was then filtered hot through a pad of dicalite
  2. washThe dicalite was washed with 300 ml hot acetonitrile
  3. customThe solvent was evaporated from the combined filtrates
  4. customgiving a waxy yellow solid
  5. customThis solid was triturated with hexanes giving 42.5 g yellow solid

Sources & evidence

ORD record
ord-8b2865146c0443e3ba750a7d433e5799
Source dataset
uspto-grants-1989_12
Patent number
US04888047

Reaction notes

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