Carbon tetrabromide → 2-[4-(2-bromo-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one

Tetrabromomethane (3.26 g, 9.82 mmol) was added to a solution of triphenylphosphine (2.58 g, 9.82 mmol) in anhydrous DMF (20 mL) at 0° C. A solution of 2-[4-(2-hydroxy-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one (1.75 g, 4.91 mmol) in DMF (7 mL) was then added dropwise and stirred the reaction mixture at room temperature for 16 hours. The solvent was removed under reduced pressure and the residue was diluted with water (50 mL) and extracted with dichloromethane (4×25 mL). The combined organic phase was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed and the solid was triturated with ether. The resulting slurry was filtered and washed with ether several times (to remove the triphenylphosphine oxide) and finally with a solution of dichloromethane-ether (1:1) to obtain 2-[4-(2-bromo-ethoxy)-3-methyl-phenyl]-5,7-dimethoxy-3H-quinazolin-4-one as an off-white solid. Yield: 0.70 g (34%).

1. customThe solvent was removed under reduced pressure
2. additionthe residue was diluted with water (50 mL)
3. extractionextracted with dichloromethane (4×25 mL)
4. washThe combined organic phase was washed with brine
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was removed
7. customthe solid was triturated with ether
8. filtrationThe resulting slurry was filtered
9. washwashed with ether several times (
10. customto remove the triphenylphosphine oxide) and finally with a solution of dichloromethane-ether (1:1)

ORD record

ord-477e37b86f15452298b48e4f60896054

Source dataset

uspto-grants-2016_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09238640B2