Tributylstannane → HCID 57479257, compound

Temperature

0 °C

Tri-n-butylstannane (ALDRICH, 0.40 ml) was added dropwise, with vigorous stirring, to a solution of lithium diisopropylamide (ALDRICH, 0.75 ml) in dry THF (3 ml) at 0° C. After stirring for 20 minutes a solution of 2-chloro-5-nonylpyrimidine (ALFA, 0.200 g) in THF (3 ml) was added dropwise at −78° C., under argon atmosphere. After 1 hour at −78° C. the cooling bath was removed and the reaction mixture warmed up to 0° C. The mixture was stirring for 3 hours at 0° C., then quenched with saturated NH4Cl (10 ml), diluted, extracted with ethyl acetate (3×10 ml), dried over MgSO4, concentrated under vacuum and purified by column chromatography on silica gel, eluting with hexane to afford 0.5 g of the title compound as a yellow oil. Although the material obtained contained a small amount of 5-nonyl-pyrimidine, it was used for the next step without further purification.

1. additionwas added dropwise at −78° C., under argon atmosphere
2. customAfter 1 hour at −78° C. the cooling bath was removed
3. customquenched with saturated NH4Cl (10 ml)
4. additiondiluted
5. extractionextracted with ethyl acetate (3×10 ml)
6. dry with materialdried over MgSO4
7. concentrationconcentrated under vacuum
8. custompurified by column chromatography on silica gel
9. washeluting with hexane

ORD record

ord-ff7faa549b104818b5845c0611d211a3

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07579353B2