2-Bromo-1-(4-hydroxyphenyl)ethanone → HCID 24864011, compound

Temperature

110 °C

748 mg (corresponding to 3.5 mmol) of 2-bromo-4′-hydroxyacetophenone and 605 mg (corresponding to 3.5 mmol) of 2-amino-5-bromopyrimidine were dissolved in 30 mL of acetonitrile. The resulting solution was refluxed in an oil bath at 110° C. for 5 hours. After the completion of the reaction, the reaction solution was cooled down to room temperature, and precipitates were filtered and recovered. The precipitates were washed with acetonitrile and dried under reduced pressure. The resulting crude crystals were suspended in a mixed solution of 10 mL of water and 15 mL of methanol. Then, about 10 mL of a saturated sodium hydrogencarbonate solution was added thereto, and the mixture was sonicated for 5 minutes using an ultrasonic washing machine. Precipitates were filtered and recovered from the resulting mixture, sufficiently washed with water, and dried under reduced pressure. The resulting crude product was recrystallized from N,N-dimethylformamide, to obtain 289 mg (corresponding to 0.997 mmol) of 6-bromo-2-(4′-hydroxyphenyl)imidazo[1,2-a]pyrimidine (FIG. 6, Step 2).

1. customAfter the completion of the reaction
2. temperaturethe reaction solution was cooled down to room temperature
3. customprecipitates
4. filtrationwere filtered
5. customrecovered
6. washThe precipitates were washed with acetonitrile
7. customdried under reduced pressure
8. additionThen, about 10 mL of a saturated sodium hydrogencarbonate solution was added
9. customthe mixture was sonicated for 5 minutes
10. customPrecipitates
11. filtrationwere filtered
12. customrecovered from the resulting mixture
13. washsufficiently washed with water
14. customdried under reduced pressure
15. customThe resulting crude product was recrystallized from N,N-dimethylformamide

ORD record

ord-f6ef62a2f0c34adb9436344abf29c9ec

Source dataset

uspto-grants-2011_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08022207B2