Phosphorus oxychloride → HCID 86036625, compound

Participants

Reaction Steps

Preparation D12, Step 3: A suspension of 6-(pyridin-2-yl)quinazolin-4-ol (106 mg, 0.47 mmol) in phosphorous oxychloride (15 mL) was heated at reflux for 1.5 h, during which time a clear, amber solution was observed. The solution was cooled to room temperature, concentrated in-vacuo, and stripped 2× from 30 mL methylene chloride to remove any remaining phosphorous oxychloride. The residue was partitioned between EtOAc and saturated sodium bicarbonate, and the mixture was stirred for 10 min. The layers were separated, and the organic phase was washed successively with saturated sodium bicarbonate, water, and brine, dried over sodium sulfate, then concentrated in-vacuo. The residue was purified over silica gel, eluting with methylene chloride followed by 1:1 methylene chloride/EtOAc, to yield 105 mg of 4-chloro-6-(pyridin-2-yl)quinazoline as a white solid. MS (ES+)=242 (M+H+).

Provenance & Evidence