Reaktion #62365

Reaktionsgleichung

trimethyl aluminum

water

5-bromo-2,4-dichloropyrimidine

potassium sodium tartrate tetrahydrate

→

title compound

Ausbeute 35.1%

5-Bromo-2-chloro-4-methylpyrimidine

Ausbeute 35.1%

Lösungsmittel

n-hexane

tetrahydrofuran

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGstirred at 80° C., under nitrogen atmosphere for 7 hours
2. 2
   workup.STIRRINGstirred at room temperature for 1 hour
3. 3
   ExtraktionThen the solution was extracted twice with ethyl acetate
4. 4
   Waschenthe resultant organic layer was washed with saturated brine
5. 5
   TrocknenAfter drying over magnesium sulfate
6. 6
   Sonstigethe solvent was evaporated
7. 7
   Sonstigepurification and isolation by silica gel column chromatography (ethyl acetate:n-hexane=1:8)

Vorschrift

5 g of 5-bromo-2,4-dichloropyrimidine was dissolved in 70 mL of tetrahydrofuran, and under stirring at room temperature, 15.8 g of trimethyl aluminum in 15% n-hexane and 1.77 g of tetrakis(triphenyl)phosphine were added, and stirred at 80° C., under nitrogen atmosphere for 7 hours. Under ice cooling, 70 mL of water was added little by little, followed by 46 g of potassium sodium tartrate tetrahydrate, and stirred at room temperature for 1 hour. Then the solution was extracted twice with ethyl acetate, and the resultant organic layer was washed with saturated brine. After drying over magnesium sulfate, the solvent was evaporated, and purification and isolation by silica gel column chromatography (ethyl acetate:n-hexane=1:8) were followed, to obtain 1.6 g of the title compound as a pale yellow syrup.

Quelle