1,3-Dimethylimidazolium Iodide → (2-Fluoro-phenyl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone

HRID 1946976Notes

Reaction equation

HRID 1946976 reaction equation
[H-].[Na+].Cl[C:4]1[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH3:11])[N:5]=1.[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].[I-].C[N+]1C=CN(C)C=1>O1CCOCC1>[F:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]([C:4]1[CH:9]=[CH:8][N:7]=[C:6]([S:10][CH3:11])[N:5]=1)=[O:16]

Participants

6

Reactant 4

HCID 203341,3-Dimethylimidazolium IodideHCID 24758Sodium hydrideHCID 67970o-FluorobenzaldehydeHCID 971134-Chloro-2-methylthiopyrimidine

Product 1

HCID 59743427(2-Fluoro-phenyl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanoneYield 27.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Sodium hydride (60% dispersion in mineral oil, 598 mg, 14.94 mmol) was added to a stirring solution of 4-chloro-2-methylthiopyrimidine (1.45 mL, 12.45 mmol), 2-fluorobenzaldehyde (1.57 mL, 14.94 mmol) and 1,3-dimethylimidazolium iodide (517 mg, 4.15 mmol) (prepared as described in Org. Synth. (1986) 64:9) in 1,4-dioxane (20 mL). The resulting mixture was heated at reflux for 1 hour; it was then cooled and partitioned between EtOAc and water. The organic layer was separated and dried over Na2SO4, filtered and evaporated under reduced pressure. The crude residue was purified by flash chromatography (hexane/EtOAc, 95/5) to give 840 mg of (2-fluorophenyl)-(2-methylsulfanyl-pyrimidin-4-yl)-methanone.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperatureit was then cooled
  4. custompartitioned between EtOAc and water
  5. customThe organic layer was separated
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customThe crude residue was purified by flash chromatography (hexane/EtOAc, 95/5)

Sources & evidence

ORD record
ord-99eb2ccdf4e7442fb75b285215c4c38d
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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