Reaction #792217

Reaction equation

DMF

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

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

cesium carbonate

→

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

Solvents

water

Conditions

Workup

1. 1
   OtherThe entire reaction mixture
2. 2
   Temperaturewas then cooled to room temperature
3. 3
   ExtractionThe reaction mixture was then extracted with ethyl acetate
4. 4
   OtherThe organic phase was separated off
5. 5
   Otherdried
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by chromatography on silica gel

Procedure

10 ml of DMF were added to 515.5 mg (3.55 mmol) of 3-(1H-pyrazol-3-yl)pyridine (preparation cf. WO 94/29300 A1), 838.5 mg (3.55 mmol) of 2-(6-bromopyridin-2-yl)pyrimidine (WO 2010/006713), 28.2 mg (0.35 mmol) of copper(II) oxide, 2.31 g (7.10 mmol) of cesium carbonate and 276.3 mg (1.06 mmol) of iron(III) acetylacetonate, and the mixture was stirred at 90° C. for 60 hours. The entire reaction mixture was then cooled to room temperature, and water was added. The reaction mixture was then extracted with ethyl acetate. The organic phase was separated off, dried and concentrated under reduced pressure. The residue was purified by chromatography on silica gel. This gave 334 g (31.3% of theory) of 2-{6-[3-(pyridin-3-yl)-1H-pyrazol-1-yl]pyridin-2-yl}pyrimidine.

Source