5-Bromo-2,4-dichloropyrimidine → (6-Bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanol

Temperature

-30 °C

To a stirred solution of 5-bromo-2,4-dichloropyrimidine (11.4 g, 50 mmol) in THF (200 mL) at −30° C., was added dropwise isopropyl magnesium chloride (25 mL, 2 M in THF, 50 mmol) and the mixture was stirred at −30° C. for 20 minutes. Then a solution of 6-bromopicolinaldehyde (9.3 g, 50 mmol) in THF (10 mL) was added and the mixture was warmed to 0° C. and stirred for another 40 minutes. The reaction was quenched by adding saturated aqueous NH4Cl solution and the resulting mixture was extracted with ethyl acetate (3×300 mL). The organic solutions were then washed with brine. The organic phase was dried with anhydrous MgSO4, filtered and concentrated under reduced pressure to give crude (6-bromo-pyridin-2-yl)-(2,4-dichloro-pyrimidin-5-yl)-methanol as a light yellow oil. (Yield 16.1 g)

1. temperaturethe mixture was warmed to 0° C.
2. stirringstirred for another 40 minutes
3. customThe reaction was quenched
4. additionby adding saturated aqueous NH4Cl solution
5. extractionthe resulting mixture was extracted with ethyl acetate (3×300 mL)
6. washThe organic solutions were then washed with brine
7. dry with materialThe organic phase was dried with anhydrous MgSO4
8. filtrationfiltered
9. concentrationconcentrated under reduced pressure

ORD record

ord-676bf3c3d6ee45d895758471fa149978

Source dataset

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08362023B2