Urea → 2,7-Dichloro-6-fluoroquinazoline

Temperature

180 °C

A mixture of 2-amino-4-chloro-5-fluorobenzaldehyde (0.30 g, 1.73 mmol) and urea (1.04 g, 17.3 mmol) was heated to 180° C. for 1 h, then cooled to RT. The solid was then suspended in a mixture of EtOAc and water and then it was filtered and the collected solid was washed with water several times, then air-dried. This intermediate quinazolinone was then suspended in phosphorus oxychloride (3.0 mL, 32.2 mmol) and then heated to 100° C. for 1 h. After cooling to RT, the mixture was added dropwise to an ice-water mixture. The mixture was stirred for 5 minutes and then the product was extracted into EtOAc (3×). The combined extracts were dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give an oil that was purified by silica gel chromatography to give 2,7-dichloro-6-fluoroquinazoline as a white solid (46 mg, 12% yield). m/z=217 (M+1).

1. temperaturecooled to RT
2. filtrationit was filtered
3. washthe collected solid was washed with water several times
4. customair-dried
5. temperatureheated to 100° C. for 1 h
6. temperatureAfter cooling to RT
7. extractionthe product was extracted into EtOAc (3×)
8. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
9. filtrationfiltered
10. concentrationconcentrated in vacuo
11. customto give an oil that
12. customwas purified by silica gel chromatography

ORD record

ord-b2872013beb34d868a81ac5df0441d31

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09303028B2