Reaction #792215

Reaction equation

2-(6-ethynylpyridin-2-yl)pyrimidine

sodium

L-ascorbic acid

3-azidopyridine

→

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

Yield 10.4%

Solvents

water

water

tert-butanol

Conditions

Workup

1. 1
   workup.ADDITIONwere added
2. 2
   Extractionextracted repeatedly with dichloromethane
3. 3
   DryingThe separated organic phases were then dried over magnesium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated
6. 6
   OtherChromatographic purification

Procedure

100 mg (833 μmol) of 3-azidopyridine (for preparation see U.S. Pat. No. 4,775,762, CAUTION explosive!) and 151 mg (833 μmol) of 2-(6-ethynylpyridin-2-yl)pyrimidine were initially charged in a mixture of 1 ml of water and 1 ml of tert-butanol, 16.5 mg (83.3 μmol) of the sodium salt of L-ascorbic acid and 20.8 mg (83.3 μmol) of copper(II) sulfate pentahydrate were added, and the mixture was stirred at room temperature for 23 hours. The reaction mixture was then added to water and extracted repeatedly with dichloromethane. The separated organic phases were then dried over magnesium sulfate, filtered and concentrated. Chromatographic purification gave 26.0 mg (10% of theory) of 2-{6-[1-(pyridin-3-yl)-1H-1,2,3-triazol-4-yl]pyridin-2-yl}pyrimidine.

Source