Sodium hydride → 1-(Pyrazin-2-yl)-1H-imidazole-4-carbaldehyde

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Sodium hydride (60% in oil, 720 mg, 18.0 mmol) was added to a 0° C. solution of 1H-imidazole-4-carboxaldehyde (2.20 g, 18.0 mmol) in DMF (8 mL). After stirring for 20 min at 0° C., the mixture was allowed to warm to RT and a solution of 2-chloropyrazine (2.06 g, 17.9 mmol) in DMF (4 mL) was added. The resulting mixture was heated to 100° C. for 18 h. The solvent was evaporated, the residue was dissolved in ethyl acetate, washed with water and brine, dried (MgSO4), and concentrated to provide 3.10 g (86%) of the title compound. MS 175 (M+H)+

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