Tributyltin Chloride → 4-Chloro-6-(tributylstannyl)thieno[3,2-d]pyrimidine

Participants

Reaction Conditions

Reaction Steps

To a flame dried flask was placed a suspension of compound 6.2 (5.92 mmol) in THF (50 mL). The reaction was cooled to −78° C. and a solution of LDA (3.25 mL of a 2.0 M solution in heptane/THF/ethyl benzene) was slowly added. After stirring for 30 minutes, a −78° C., a solution of (n-Bu)3SnCl (1.9 mL) in THF (50 mL) was added via cannula over a 20 minute period at −78° C. and stirred for 2 hours. The reaction was warmed to room temperature, hydrolyzed with saturated NH4Cl, extracted with EtOAc, dried and concentrated. The crude product was purified by flash column chromatography on silica gel (1:1 hexanes/dichloromethane then 10% EtOAc/dichloromethane) to provide 4-chloro-6-tributylstannanyl-thieno[3,2-d]pyrimidine (compound 52.1) in 92% yield.

Provenance & Evidence