反应详情

温度

110 °C

2-(4-iodo-2-pyridyl)-2-methyl-propanenitrile (100 mg, 0.3675 mmol), PdCl2(PCy3)2 (20.87 mg, 0.02827 mmol), 4,4,5,5-tetramethyl-2-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,3,2-dioxaborolane (96.90 mg, 0.3816 mmol), potassium acetate (83.23 mg, 0.8481 mmol) in 1,4-dioxane (1.615 mL). The reaction mixture was degassed with 5× vacuum/nitrogen cycles then heated at 110° C. for 4 hours. 3-amino-6-bromo-pyrazine-2-carbohydrazide (65.60 mg, 0.2827 mmol), potassium carbonate (136.7 mg, 0.9894 mmol), [PdCl2(dppf)].dichloromethane (23.09 mg, 0.02827 mmol) and water (0.89 mL) was added and the mixture was heated at 100° C. for 18 hours. The reaction mixture was concentrated in vacuo. The residue was partitioned between dichloromethane and water. Combined organic extract were dried over MgSO4 and concentrated in vacuo yielding an oil. Purified by silica gel chromatography eluted with 5% methanol/dichloromethane. Product fractions were combined and concentrated in vacuo to yield 3-amino-6-[2-(1-cyano-1-methyl-ethyl)-4-pyridyl]pyrazine-2-carbohydrazide as a beige solid (49.5 mg, 57.1%) LC/MS m/z 298.1 [M+H]+.

1. customThe reaction mixture was degassed with 5× vacuum/nitrogen cycles
2. temperaturethe mixture was heated at 100° C. for 18 hours
3. concentrationThe reaction mixture was concentrated in vacuo
4. customThe residue was partitioned between dichloromethane and water
5. extractionCombined organic extract
6. dry with materialwere dried over MgSO4
7. concentrationconcentrated in vacuo
8. customyielding an oil
9. customPurified by silica gel chromatography
10. washeluted with 5% methanol/dichloromethane
11. concentrationconcentrated in vacuo