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

Temperatur

-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-Eintrag

ord-676bf3c3d6ee45d895758471fa149978

Quelldatensatz

uspto-grants-2013_01

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US08362023B2