Reaktion #1938381

Reaktionsgleichung

5-chloro-2-isopropyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine

4-formylphenylboronic acid

sodium carbonate

→

4-(2-Isopropyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidin-5-yl)benzaldehyde

Lösungsmittel

1,2-dimethoxyethane

water

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeseparating
2. 2
   Extraktionthe phases and extraction of the aqueous phase with dichloromethane
3. 3
   TrocknenThe combined organic layers were dried over sodium sulphate
4. 4
   Sonstigethe solvent was evaporated
5. 5
   FiltrationThe insoluble solid was filtered
6. 6
   Sonstigethe filtrate was evaporated
7. 7
   SonstigeThe residue was purified by chromatography on silica gel (dichloromethane/ethyl acetate)
8. 8
   Sonstigeto yield the product

Vorschrift

To a mixture of 5.30 g 5-chloro-2-isopropyl-6-phenyl[1,2,4]triazolo[1,5-a]pyrimidine and 3.80 g 4-formylphenylboronic acid in 160 mL 1,2-dimethoxyethane were added 33 mL of a 10% w/w sodium carbonate solution and 0.71 g dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium (II) and the resulting mixture was heated to 90° C. under an inert gas atmosphere for 18 h. The work up was performed by diluting the reaction mixture with water and dichloromethane, separating the phases and extraction of the aqueous phase with dichloromethane. The combined organic layers were dried over sodium sulphate, the solvent was evaporated and the residue suspended in ethyl acetate. The insoluble solid was filtered and the filtrate was evaporated. The residue was purified by chromatography on silica gel (dichloromethane/ethyl acetate) to yield the product.

Quelle