N,N-Dimethylaniline → 8-Bromo-4-chloro-2-methylquinazoline

Temperature

80 °C

Part C: To a suspension of 14.2 g (59.5 mmol) of 2-methyl-4-hydroxy-8-bromo-quinazoline in 300 ml of benzene, 16 ml (120 mmol) of dimethylaniline and 6 ml (64 mmol) of phosphorus oxychloride were added under nitrogen. The light yellow solution resulting after heating to 80° C. while stirring was further heated at 80° C. for 3 hours. After cooling to room temperature 500 ml of benzene were added. The solution was extracted three times with 300 ml of 20% NaOH/water and 200 ml of water. The organic layer was dried over magnesium sulphate and concentrated in vacuo. The product was purified by column chromatography over silicagel using ether/petroleum-ether 1:9 as the eluent. A total of 12.3 g of 2-methyl-4-chloro-8-bromo-quinazoline was obtained as a white solid (80% yield).

1. additionwere added under nitrogen
2. customThe light yellow solution resulting
3. temperaturewas further heated at 80° C. for 3 hours
4. additionwere added
5. extractionThe solution was extracted three times with 300 ml of 20% NaOH/water and 200 ml of water
6. dry with materialThe organic layer was dried over magnesium sulphate
7. concentrationconcentrated in vacuo
8. customThe product was purified by column chromatography

ORD record

ord-2f3530b465d542b38880a12f22988e81

Source dataset

uspto-grants-2002_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06350750B1