Reaction #1442491

Reaction equation

tri-n-butylstannylthiophene

4,6-dichloropyrimidine

→

product

Yield 72.0%

4,6-Di(thien-2-yl)pyrimidine

Yield 72.0%

Solvents

toluene

Conditions

Workup

1. 1
   TemperatureThe reaction mixture was refluxed for 6 hours
2. 2
   Temperatureafter cooling
3. 3
   Othera white precipitate was formed in the reaction flask
4. 4
   OtherThe solid was collected
5. 5
   workup.ADDITIONthe organic phase was diluted with ether (100 mL)
6. 6
   workup.ADDITIONpoured onto a solution of NH4F (3 g, 100 ml)
7. 7
   Otherseparated
8. 8
   DryingAfter drying over MgSO4
9. 9
   Otherthe solvent was evaporated
10. 10
    Otheraffording a solid material
11. 11
    Othercrystallized from toluene

Procedure

A mixture of tri-n-butylstannylthiophene (10.52 g, 28.19 mmol), 4,6-dichloropyrimidine (2.00 g, 13.42 mmol), tetrakis(triphenylphosphine)palladium(0) (0.345 g, 0.30 mmol) and few crystals of 2,6-di-tert-butyl-4-methylphenolo in dry toluene (20 mL) was deareated twice with nitrogen. The reaction mixture was refluxed for 6 hours and, after cooling, a white precipitate was formed in the reaction flask. The solid was collected and the organic phase was diluted with ether (100 mL), poured onto a solution of NH4F (3 g, 100 ml) and separated. After drying over MgSO4, the solvent was evaporated affording a solid material. The two solid phase were combined and crystallized from toluene to give the pure product as a white crystals (2.36 g, 9.66 mmol, 72.0% yield). mp 146° C.; 1H NMR (CDCl3) δ 9.07 (1H, d, 2J=1.4), 7.86 (1H, d, 2J=3.7), 7.83 (1H, d), 7.57 (1H, d, 2J=5.1), 7.20 (1H, dd).

Source