Tert-Butylamine → HCID 90041146, compound

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Reaction Steps

A mixture of 2-bromo-3-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1.16 g, 3 mmol), HBTU [1-[bis(dimethylamino)methylene]-1H-benzotriazolium 3-oxide, hexafluorophosphate(1-) (1:1) (1.48 g, 3.9 mmol), N,N-dimethylformamide (12 mL) and triethylamine (0.61 g, 6 mmol) was stirred at room temperature for 1 h, and then tert-butylamine (0.63 mL, 6 mmol) was added. The mixture was stirred an additional hour and then diluted with ethyl acetate, washed once with 0.5 M sodium carbonate, twice with water, once with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by chromatography (silica, 20% ethyl acetate in hexanes) gave 2-bromo-3-methyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid tert-butylamide (1.22 g, 92%) as a white crystalline solid. 1H NMR (400 MHz, DMSO-d6) δ ppm −0.09 (s, 9H), 0.83 (t, J=8.2 Hz, 2H), 1.43 (s, 9H), 2.71 (s, 3H), 3.54 (t, J=8.2 Hz, 2H), 5.64 (s, 2H), 7.64 (s, 1H), 8.49 (s, 1H).

Provenance & Evidence