Reaktion #2002741

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 are dried over sodium sulphate
4. 4
   Sonstigethe solvent is evaporated
5. 5
   FiltrationThe insoluble solid is filtered
6. 6
   Sonstigethe filtrate is evaporated
7. 7
   SonstigeThe residue is 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 are 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 is heated to 90° C. under an inert gas atmosphere for 18 h. The work up is 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 are dried over sodium sulphate, the solvent is evaporated and the residue suspended in ethyl acetate. The insoluble solid is filtered and the filtrate is evaporated. The residue is purified by chromatography on silica gel (dichloromethane/ethyl acetate) to yield the product.

Quelle