2-Chloropyrimidine → HCID 86669123, compound

Participants

Reaction Steps

N-BuLi [2.5M in hexane] (4 ml, 10 mmol) added at −78° C. to a solution of N,N-dimethyl imidazole-1-sulphonamide (1.75 g, 10 mmol) in dry ether (60 ml), stirred 1 hour, anion transferred to a suspension of 2-chloropyrimidine (1.48 g, 10 mmol) in ether (80 ml) keeping the temperature -30° C., temperature brought to 0° C. and held for 30 min. Reaction quenched with AcOH (0.64 ml) and water (0.1 ml), to the reaction was added THF (2 ml) then DDQ (2.27 g) in THF (10 ml) and stirred 0/N. Reaction diluted with EtOAc, solid filtered off and filtrate washed with water (3×) then ice cold 0.5% NaOH, organic layer dried over MgSO4, filtered and concentrated under reduced pressure, residue was purified by column chromatography to give the product (130 mg).

Provenance & Evidence