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

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Reaction Conditions

Reaction Steps

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)

Provenance & Evidence