Réaction #792212

Équation de réaction

3-(1H-pyrazol-4-yl)pyridine

2-(6-bromopyridin-2-yl)pyrimidine

potassium carbonate

→

2-{6-[4-(Pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine

Solvants

DMF

Conditions de réaction

Traitement

1. 1
   AutreThe entire reaction mixture
2. 2
   Concentrationwas then concentrated under reduced pressure
3. 3
   Autregave
4. 4
   Autrean alkaline reaction (pH=9)
5. 5
   Extractionthe mixture was extracted four times with ethyl acetate
6. 6
   Séchagethe combined organic phases were dried with sodium sulfate
7. 7
   Concentrationconcentrated under reduced pressure
8. 8
   AutreThe residue was purified by chromatography on silica gel (mobile phase: cyclohexane/acetone)

Mode opératoire

DMF was added to 0.8 g (5.5 mmol) of 3-(1H-pyrazol-4-yl)pyridine (Angew. Chemie, 2006, 118 (8) 1304), 1.3 g (5.5 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine (WO 2010/006713), 0.29 g (0.82 mmol) of copper-8-hydroxyquinoline complex (cf. Tetrahedron Lett, 2006, 149) and 2.28 g (16.5 mmol) of potassium carbonate, and the mixture was stirred at 120° C. under argon for 16 hours. The entire reaction mixture was then concentrated under reduced pressure. The residue was admixed with aqueous citric acid, aqueous sodium chloride, ethyl acetate and diluted aqueous sodium hydroxide solution until the mixture gave an alkaline reaction (pH=9), the mixture was extracted four times with ethyl acetate and the combined organic phases were dried with sodium sulfate and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (mobile phase: cyclohexane/acetone). This gave 0.56 g (32% of theory) of 2-{6-[4-(pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine.

Source