1,3-Dimethylimidazolium Iodide → (2-Bromo-3-methylphenyl)(2-(methylthio)pyrimidin-4-yl)methanone

HRID 1028976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1028976
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1.[Br:10][C:11]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:12]=1[CH:13]=[O:14].[I-].CN1C=C[N+](C)=C1.[H-].[Na+]>C1COCC1>[Br:10][C:11]1[C:18]([CH3:19])=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]([C:2]1[CH:7]=[CH:6][N:5]=[C:4]([S:8][CH3:9])[N:3]=1)=[O:14]

Komponenten

6

Edukt 4

HCID 203341,3-Dimethylimidazolium IodideHCID 24758Sodium hydrideHCID 971134-Chloro-2-methylthiopyrimidineHCID 137070762-Bromo-3-methylbenzaldehyde

Produkt 1

HCID 67325293(2-Bromo-3-methylphenyl)(2-(methylthio)pyrimidin-4-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a mixture of 4-chloro-2-(methylthio)pyrimidine (0.36 mL, 3.11 mmol), 2-bromo-3-methylbenzaldehyde (0.744 g, 3.74 mmol), and 1,3-dimethyl-1H-imidazol-3-ium iodide (0.697 g, 3.11 mmol) in THF (3 mL) was added NaH (0.149 g, 3.74 mmol) and the resulting mixture was refluxed for 30 min. Product was observed and the reaction went to completion. The mixture was brought to RT and poured into ice-water, extracted with DCM and purified using hexanes to afford a light yellow solid as (2-bromo-3-methylphenyl)(2-(methylthio)pyrimidin-4-yl)methanone.

Aufarbeitung

  1. temperaturethe resulting mixture was refluxed for 30 min
  2. customwas brought to RT
  3. extractionextracted with DCM
  4. custompurified

Quellen und Nachweise

ORD-Eintrag
ord-bd757552015a4997a8dd58608e5fd8c9
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735384B2

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