Ammonium Chloride → HCID 19021674, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of lithium t-butoxide (5.2 g, 65 mmol) in anhydrous THF (150 mL) is treated with cuprous iodide (12.4 g, 65 mmol) at room temperature under a nitrogen atmosphere and stirred for 1 h. The mixture is cooled to -78° C., treated with 2M ethylmagnesium bromide (32.5 mL, 65 mmol) and stirred for 20 min. A pre-cooled solution (-78° C.) of 2,4-dichloro-5-nitropyrimidine (9.7 g, 50 mmol) in THF (30 mL) is added via canula. The mixture is stirred for 2 h at -78° C. then a 1:1 mixture of saturated aqueous solution of NH4Cl and ether (1000 mL) is added and stirred for 1 h. The reaction mixture is extracted with ether (2×200 mL). The organic phase is washed with 50 mL of 1N HCl, followed by saturated NaHCO3 and brine. Drying over MgSO4 and concentration in vacuo is followed by flash column chromatography on silica gel which affords material to which is added 20 mL acetonitrile then a solution of 2-ethyl-4-methyl imidazole (5.4 g, 49 mmol) in acetonitrile (40 mL). The mixture is allowed to stir for 15 h at room temperature. The solvent is evaporated and the solid is subjected to flash chromatography on silica gel with CH2Cl2 :MeOH (19+1) as eluent to afford the title compound.

Provenance & Evidence