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Stage #1: 3-bromo-5-iodopyrazin-2-amine With sodium hydroxide In acetone at 20℃; for 0.333333h;
Stage #2: C10H10NO2PolS In tetrahydrofuran; acetone at 20℃; for 8h;
(Z)-N,N-dimethyl-N′-[3-bromo-5-(trifluoromethyl)-2-pyrazinyl]methanimidamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With copper (I) iodide; lithium iodide at 100℃; for 12h; Sealed tube; Schlenk technique;
(Z)-N,N-Dimethyl-N′-(pyrazin-2-yl)formimidamides 5; GeneralProcedure
General procedure: 2-Aminopyrazine 1 (0.10 mmol), LiI (2a) (0.10 mmol) and Selectfluor(3) (0.10 mmol) were dissolved in DMF (2 mL) in a sealed tube, andthe resulting mixture was stirred at 15 °C for 3 h. The mixture wasdiluted with aqueous NaCl solution, extracted with EtOAc (3 × 10 mL),and the combined organic layer was dried over Na2SO4. After concentrationof the filtrate, the residue was dissolved in DMF (2 mL) in asealed tube. CuI (15 mol%) and FSO2CF2CO2Me (4) (0.3 mmol) wereadded and the resulting mixture was stirred at 100 °C for 12 h. Themixture was diluted with aqueous NaCl solution and extracted withEtOAc (3 × 10 mL). The combined organic layer was then dried overNa2SO4 and filtered. After concentration of the filtrate, purification ofthe residue by column chromatography on silica gel (petroleumether/EtOAc, 10:1 to 5:1) gave the desired product 5
With copper (I) iodide at 100℃; for 12h; Sealed tube; Schlenk technique;
(Z)-N,N-Dimethyl-N′-(pyrazin-2-yl)formimidamides 5; GeneralProcedure
General procedure: 2-Aminopyrazine 1 (0.10 mmol), LiI (2a) (0.10 mmol) and Selectfluor(3) (0.10 mmol) were dissolved in DMF (2 mL) in a sealed tube, andthe resulting mixture was stirred at 15 °C for 3 h. The mixture wasdiluted with aqueous NaCl solution, extracted with EtOAc (3 × 10 mL),and the combined organic layer was dried over Na2SO4. After concentrationof the filtrate, the residue was dissolved in DMF (2 mL) in asealed tube. CuI (15 mol%) and FSO2CF2CO2Me (4) (0.3 mmol) wereadded and the resulting mixture was stirred at 100 °C for 12 h. Themixture was diluted with aqueous NaCl solution and extracted withEtOAc (3 × 10 mL). The combined organic layer was then dried overNa2SO4 and filtered. After concentration of the filtrate, purification ofthe residue by column chromatography on silica gel (petroleumether/EtOAc, 10:1 to 5:1) gave the desired product 5
With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); lithium iodide In N,N-dimethyl-formamide at 15℃; for 3h; Sealed tube; Schlenk technique; regioselective reaction;
(Z)-N,N-Dimethyl-N′-(pyrazin-2-yl)formimidamides 5; GeneralProcedure
General procedure: 2-Aminopyrazine 1 (0.10 mmol), LiI (2a) (0.10 mmol) and Selectfluor(3) (0.10 mmol) were dissolved in DMF (2 mL) in a sealed tube, andthe resulting mixture was stirred at 15 °C for 3 h. The mixture wasdiluted with aqueous NaCl solution, extracted with EtOAc (3 × 10 mL),and the combined organic layer was dried over Na2SO4. After concentrationof the filtrate, the residue was dissolved in DMF (2 mL) in asealed tube. CuI (15 mol%) and FSO2CF2CO2Me (4) (0.3 mmol) wereadded and the resulting mixture was stirred at 100 °C for 12 h. Themixture was diluted with aqueous NaCl solution and extracted withEtOAc (3 × 10 mL). The combined organic layer was then dried overNa2SO4 and filtered. After concentration of the filtrate, purification ofthe residue by column chromatography on silica gel (petroleumether/EtOAc, 10:1 to 5:1) gave the desired product 5
With 1-(chloromethyl)-4-fluoro-1,4-diazoniabicyclo-[2.2.2]octane bis(tetrafluoroborate); lithium iodide In N,N-dimethyl-formamide at 15℃; for 3h; Sealed tube; Schlenk technique; regioselective reaction;
(Z)-N,N-Dimethyl-N′-(pyrazin-2-yl)formimidamides 5; GeneralProcedure
General procedure: 2-Aminopyrazine 1 (0.10 mmol), LiI (2a) (0.10 mmol) and Selectfluor(3) (0.10 mmol) were dissolved in DMF (2 mL) in a sealed tube, andthe resulting mixture was stirred at 15 °C for 3 h. The mixture wasdiluted with aqueous NaCl solution, extracted with EtOAc (3 × 10 mL),and the combined organic layer was dried over Na2SO4. After concentrationof the filtrate, the residue was dissolved in DMF (2 mL) in asealed tube. CuI (15 mol%) and FSO2CF2CO2Me (4) (0.3 mmol) wereadded and the resulting mixture was stirred at 100 °C for 12 h. Themixture was diluted with aqueous NaCl solution and extracted withEtOAc (3 × 10 mL). The combined organic layer was then dried overNa2SO4 and filtered. After concentration of the filtrate, purification ofthe residue by column chromatography on silica gel (petroleumether/EtOAc, 10:1 to 5:1) gave the desired product 5
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