Tributyltin azide → HCID 178477998, compound

Participants

Reaction Conditions

Reaction Steps

The title compound is prepared starting from 4-{4-[3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-benzonitrile. 4-{4-[3-(4-chloro-phenyl)-1H-pyrazol-4-yl]-pyrimidin-2-ylamino}-benzonitrile (0.932 g; 2.5 mMol) is suspended in o-xylene (10 mL) and treated at rt with azidotributyltin (1.66 g; 1.37 mL; 5 mMol). After stirring the yellow suspension at 160° C. for 117 h the reaction mixture is filtered off without cooling and the crystals are washed with o-xylene. Since the reaction is still incomplete, the crude product is resuspended in o-xylene (20 mL) and treated at rt with azidotributyltin (1.37 mL; 5 mMol). After stirring the yellow suspension at 160° C. for 117 h the reaction mixture is filtered off without cooling and the crystals are washed with o-xylene. The crude product is suspended in methanol (1.00 mL), refluxed and filtered without cooling. The crude product is acidified with 4N HCL/methanol and extracted with ethyl acetate. The aqueous layer is basified with 4N NaOH (ca. pH 12) and extracted with ethyl acetate. Upon this treatment, the product precipitates from the aqueous layer and is filtered off to obtain the title compound.

Provenance & Evidence