Tributylstannane → 4-Chloro-2-methyl-6-(tributylstannyl)pyrimidine

Temperatur

0 °C

n-Butyllithium solution, 1.6 M in hexane (0.184 mL, 2.200 mmol, Aldrich, St. Louis, Mo.) was added to a solution of diisopropylamine (0.314 mL, 2.200 mmol) in THF (5 mL) at 0° C. The reaction mixture was stirred at 0° C. for 15 min. Tributyltin hydride (0.527 mL, 2.000 mmol, Aldrich, St. Louis, Mo.) was added dropwisely. The solution was stirred at 0° C. for 15 min. The mixture was cooled down to −78° C., 4,6-dichloro-2-methylpyrimidine (326 mg, 2.000 mmol, Aldrich, St. Louis, Mo.) in THF (2 mL) was then added and the mixture was stirred at −78° C. for 8 h. The mixture was quenched by saturated aqueous KF (4 mL), and extracted with EtOAc (30 mL). The organic extract was washed with saturated NaCl (5 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give 4-chloro-2-methyl-6-(tributylstannyl)pyrimidine as a light-yellow oil. The crude material was used directly in the next step without purification.

1. stirringThe solution was stirred at 0° C. for 15 min
2. temperatureThe mixture was cooled down to −78° C.
3. stirringthe mixture was stirred at −78° C. for 8 h
4. customThe mixture was quenched by saturated aqueous KF (4 mL)
5. extractionextracted with EtOAc (30 mL)
6. extractionThe organic extract
7. washwas washed with saturated NaCl (5 mL)
8. dry with materialdried over Na2SO4
9. filtrationThe solution was filtered
10. concentrationconcentrated in vacuo

ORD-Eintrag

ord-180197c2179a477c8f7124f9da324c39

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08362241B2