N-bromobutanimide → Thieno[3,2-d]pyrimidine-7-carbaldehyde

A mixture of 7-methyl-thieno[3,2-d]pyrimidine (1.2 g) and N-bromosuccinimide (2.9 g) in carbon tetrachloride (50 mL) was heated at reflux for 1 hour. The reaction mixture was then cooled, the solid formed was filtered off and the filtrate was concentrated under reduced pressure. The residue was suspended in water (10 mL) and the suspension was heated at reflux for 1 hour. The resulting mixture was basified by addition of a saturated aqueous solution of sodium bicarbonate and extracted twice with dichloromethane (100 mL). The combined organic layers were washed with brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure. The solid residue was triturated with ethyl acetate and hexane and then collected by filtration to give 0.8 g of thieno[3,2-d]pyrimidine-7-carbaldehyde.

1. temperaturewas heated
2. temperatureat reflux for 1 hour
3. temperatureThe reaction mixture was then cooled
4. customthe solid formed
5. filtrationwas filtered off
6. concentrationthe filtrate was concentrated under reduced pressure
7. temperaturethe suspension was heated
8. temperatureat reflux for 1 hour
9. additionThe resulting mixture was basified by addition of a saturated aqueous solution of sodium bicarbonate
10. extractionextracted twice with dichloromethane (100 mL)
11. washThe combined organic layers were washed with brine
12. dry with materialdried over anhydrous sodium sulfate
13. filtrationfiltered
14. customevaporated under reduced pressure
15. customThe solid residue was triturated with ethyl acetate and hexane
16. filtrationcollected by filtration

ORD record

ord-2f8dfb191ba54a479e55236ad70c35e8

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09255110B2