Imidazole → (5-Nitro-pyrazin-2-yl)-(2-triethylsilanyloxy-ethyl)-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 2-(5-nitro-pyrazin-2-ylamino)-ethanol (370 mg, 2.01 mmol) in N,N-dimethylformamide (10 mL) at 0° C. was treated with chlorotriethylsilane (371 μL, 2.21 mmol) and imidazole (342 mg, 5.02 mmol). The reaction mixture was then allowed to warm up to 25° C. where it was stirred overnight for 16 h. After this time, the reaction was diluted with ethyl acetate (20 mL) and a saturated aqueous sodium chloride solution (10 mL) and then further extracted with ethyl acetate (2×10 mL). The combined organic layers were dried over sodium sulfate, filtered, and concentrated in vacuo. Biotage chromatography (FLASH 40S, Silica, 1/3 hexanes/ethyl acetate) afforded (5-nitro-pyrazin-2-yl)-(2-triethylsilanyloxy-ethyl)-amine (531 mg, 89%) as a light yellow solid: (ES)+-HRMS m/e calcd for C12H22N4O3Si (M+H)+ 299.1534, found 299.1538.

Provenance & Evidence