2-(Tributylstannyl)pyridine → HCID 178517958, compound

Participants

Reaction Steps

Preparation D12, Step 2: A mixture of 6-bromoquinazolin-4-ol (173 mg, 0.77 mmol) and 2-tributylstannylpyridine (850 mg, 2.30 mmol) in toluene (10 mL), plus a few drops of DMF to improve solubility, was degassed under vacuum/argon, then a catalytic amount of tetrakis(triphenylphosphine)palladium(0) was added, the mixture was degassed again, and then heated at reflux for 4 h. The reaction was cooled to room temperature, and some solids were removed by filtration. Analysis by LC/MS indicated that the desired product was present in both the solids and the filtrate. The solids were slurried in 8:2 methylene chloride/methanol, the mixture was filtered, the filtrate was combined with the original filtrate, and this mixture was concentrated in-vacuo. The residue was purified over silica gel, eluting with 50% EtOAc/hexanes, 75% EtOAc/hexanes, 100% EtOAc, 5% MeOH/EtOAc, to yield 106 mg of 6-(pyridin-2-yl)quinazolin-4-ol as a colorless solid. MS (ES+)=224 (M+H+).

Provenance & Evidence