反应详情

温度

25 °C

2-Bromo-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (1.12 g, 3.01 mmol) and HATU (1.37 g, 3.61 mmol) were combined with DMF (5.2 mL) then propan-2-amine (711 mg, 1.03 mL, 12.0 mmol) was added via syringe. The reaction mixture was stirred at 25° C. After 14 h, water (50 mL) was added and the mixture extracted with EtOAc (4×50 mL). The combined organics were washed with water (30 mL), saturated sodium chloride solution (3×20 mL) and dried with MgSO4. Solvents were evaporated and the residue purified by chromatography (silica, 0 to 30% EtOAc in hexanes over 15 min) to yield 2-bromo-N-isopropyl-5-((2-(trimethylsilyl)ethoxy)methyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxamide (1.17 g, 2.83 mmol, 94%) as a white solid. MS (M+Na)+=435; 1H NMR (CDCl3) δ: 8.41 (s, 1H), 8.35 (s, 1H), 7.72 (d, J=4.9 Hz, 1H), 5.65 (s, 2H), 4.19-4.45 (m, 1H), 3.41-3.69 (m, 2H), 1.34 (d, J=6.8 Hz, 6H), 0.82-0.97 (m, 2H), −0.13-0.09 (m, 9H).

1. extractionthe mixture extracted with EtOAc (4×50 mL)
2. washThe combined organics were washed with water (30 mL), saturated sodium chloride solution (3×20 mL)
3. dry with materialdried with MgSO4
4. customSolvents were evaporated
5. customthe residue purified by chromatography (silica, 0 to 30% EtOAc in hexanes over 15 min)