2-Amino-2-methyl-1-propanol → 2-Bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide

Participants

Reaction Steps

To a mixture of 2-bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (2 g, 5.37 mmol), 2-amino-2-methylpropan-1-ol (575 mg, 6.45 mmol) and HATU (2.25 g, 5.91 mmol) was added DIPEA (2.08 g, 2.81 mL, 16.1 mmol) and DMF (18 mL). The mixture was stirred at room temperature for 16 h then was diluted with EtOAc and 10% citric acid. The phases were separated and the organic phase was then washed successively with 10% citric acid, NaHCO3 and brine. The organic phase was dried (MgSO4), filtered and purified by chromatography (silica, 20-60% ethyl acetate in hexanes) to give 2-bromo-N-(1-hydroxy-2-methylpropan-2-yl)-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (1.95 g, 4.4 mmol, 82%) as a white solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm: 8.47 (s, 1H), 8.34 (s, 1H), 8.13 (s, 1H), 5.69 (s, 2H), 3.78 (s, 2H), 3.57 (t, J=8.4 Hz, 3H), 1.52 (s, 60.96 (t, J=8.4 Hz, 3H), 0.00 (s, 9H).

Provenance & Evidence