Reaction #792220

Reaction equation

2-tributylstannylthiazole

2-bromo-6-pyrimidylpyridine

→

2-[6-(1,3-Thiazol-2-yl)pyridin-2-yl]pyrimidine

Solvents

toluene

Conditions

Workup

1. 1
   OtherFor work-up, the solvent was removed under reduced pressure
2. 2
   workup.DISSOLUTIONthe crude product was dissolved in dichloromethane
3. 3
   Filtrationthe mixture was filtered through Celite
4. 4
   Concentrationthe organic phase was concentrated
5. 5
   OtherFurther purification by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate)

Procedure

Under argon, 2.69 g (7.18 mmol) of 2-tributylstannylthiazole, 1.69 g (7.18 mmol) of 2-bromo-6-pyrimidylpyridine and 0.49 g (0.43 mmol) of tetrakis(triphenylphosphine)palladium were stirred in 100 ml of toluene at 100° C. for 16 hours. For work-up, the solvent was removed under reduced pressure, the crude product was dissolved in dichloromethane and stirred with saturated potassium fluoride solution for 16 hours, the mixture was filtered through Celite and the organic phase was concentrated. Further purification by column chromatography on silica gel (mobile phase: cyclohexane/ethyl acetate). This gave 0.93 g (54% of theory) of 2-[6-(1,3-thiazol-2-yl)pyridin-2-yl]pyrimidine which was used for subsequent reactions.

Source