1-(Bromomethyl)-4-chlorobenzene → 2,4-Dichloro-6-[2-(4-chlorophenyl)ethyl]pyrimidine

Participants

Reaction Conditions

Reaction Steps

Lithium diisopropylamide (11 mL, 2 M solution in heptane/tetrahydrofuran/ethylbenzene) was added dropwise over 5 min to a solution of 2,4-dichloro-6-methylpyrimidine (3.0 g) in tetrahydrofuran (20 mL) at −78° C. under nitrogen. The reaction was stirred at −78° C. for 30 minutes. 4-Chlorobenzylbromide (4.4 g) was dissolved in tetrahydrofuran (5 mL) and added dropwise over 5 minutes. The reaction was stirred at −78° C. for 30 min, allowed to warm to rt and stirred at rt for 16 h. Solvent was removed under vacuum. The residue was purified by column chromatography (5% ethyl acetate in hexanes) to afford 2,4-dichloro-6-[2-(4-chlorophenyl)ethyl]pyrimidine, (2.8 g).

Provenance & Evidence