Reaction #792212

Reaction equation

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

Solvents

DMF

Conditions

Workup

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

Procedure

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