1-(1H-Imidazol-1-yl)-N,N-dimethylmethanamine → [4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl](1H-imidazol-2-yl)methanone

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-[(dimethylamino)methyl]-imidazole (0.70 g, 5.6 mmol) (See Katritzky, A. R.; Rewcastle, G. W.; Fan, W-Q; J. Org. Chem. 1988, 53, 5688) in tetrahydrofuran (10 mL) at -78° C. under nitrogen atmosphere is added a 1.58M solution of n-butyllithium (3.60 mL, 5.69 mmol) in hexanes dropwise. The resulting mixture is stirred 1 hour at -78° C., warmed to ~0° C., and stirred 0.5 hours. After cooling to -78° C., 4,6-bis(1,1-dimethylethyl)-5-hydroxy-N-methoxy-N-methyl-2-pyrimidinecarboxamide (0.50 g, 1.7 mmol) in tetrahydrofuran (5 mL) is added. This mixture is warmed to room temperature, stirred for 16 hours, and quenched by addition of aqueous 2N hydrochloric acid solution. After extraction with ethyl acetate, the combined extracts are washed with water and brine solution. Concentration of the organic phase under vacuum followed by recrystallization of the organic residue from methanol and water gives 0.43 g (84%) of the title compound, mp 217°-220° C.

Provenance & Evidence