Dibutyltin oxide → HCID 178490276, compound

Participants

Reaction Steps

A solution of 3-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-benzonitrile [0.12 g, 0.33 mmol, Example 35(t)], trimethylsilylazide (0.22 mL, 1.65 mmol) and dibutyltinoxide (41 mg, 0.16 mmol) in toluene (5 mL) is heated to 95° C. for 6 hours. The reaction mixture is concentrated, and partitioned between water and ethyl acetate. The aqueous phase solution is acidified with dilute hydrochloric acid to pH, 3.0, and extracted with ethyl acetate. The extracts are dried over magnesium sulfate, filtered and concentrated. The residue is subjected to chromatography on silica gel eluting with 5% MeOH in DCM to afford [2-(4-methoxy-phenyl)-ethyl]-{2-methoxy-6-[3-(1H-tetrazol-5-yl)-phenyl]-pyrimidin-4-yl}-amine [60 mg, 45%, Example 24(a)]. LCMS: RT=2.65 minutes, MS: 404 (M+H).

Provenance & Evidence