N,N-Dimethylaniline → 4-chloro-2-(3-pyridyl)quinazoline

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Reaction Steps

A solution of the quinazolinone compound (6.7 g, prepared in Reference example 7) and 5.7 mL of N,N-dimethylaniline in 200 mL of benzene was heated to reflux, under nitrogen atmosphere, for one-half hour with the removal of 15 mL of distillate. After cooling to room temperature, phosphorus oxychloride (4.5 g) was added and the resulting solution heated to reflux for six hours. After cooling to room temperature, the solution was washed with ice water and dilute sodium hydroxide solution. The organic extract was dried over sodium sulfate and concentrated under reduced pressure. The concentrate was triturated in ether and collected to give the title compound (3.0 g) having the following physical data.

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