5-Bromo-2,4-dichloropyrimidine → (2,4-Dichloro-pyrimidin-5-yl)-(2,3-difluoro-6-methoxy-phenyl)-methanol

Temperature

0 °C

To a stirred solution of 5-bromo-2,4-dichloropyrimidine (Aldrich, 3.02 g, 13.25 mmol) in 20 mL of THF at −30° C., isopropyl magnesium chloride (Aldrich, 2M solution in THF, 7.12 mL, 13.25 mmol) was added dropwise and the mixture was stirred for 20 minutes. Then 2,3-difluoro-6-methoxy-benzaldehyde (Matrix, 2.28 g, 13.25 mmol) was added and the mixture was warmed to 0° C. and stirred for 40 minutes. The reaction was quenched with saturated ammonium chloride solution and the resulting mixture was extracted with EtOAc. The extract was dried with sodium sulfate. The solvent was removed on a rotary evaporator and the solid was treated with hexane (8 mL). The solid was filtered and dried to give an off-white solid. 3.42 g; Yield, 80.5%. MS (M+H)+, 322.

1. stirringstirred for 40 minutes
2. customThe reaction was quenched with saturated ammonium chloride solution
3. extractionthe resulting mixture was extracted with EtOAc
4. dry with materialThe extract was dried with sodium sulfate
5. customThe solvent was removed on a rotary evaporator
6. additionthe solid was treated with hexane (8 mL)
7. filtrationThe solid was filtered
8. customdried
9. customto give an off-white solid
10. customYield

ORD record

ord-9dcc2cfd066a499d8e93596560645710

Source dataset

uspto-grants-2008_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07405220B2