Dichloromethane → 3-Amino-6-[2-(1-cyano-1-methyl-ethyl)-4-pyridyl]pyrazine-2-carbohydrazide

Participants

Reaction Conditions

Reaction Steps

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]+.

Provenance & Evidence