3,5-DICHLOROPYRAZINE-2-CARBOXAMIDE

To a mixture of 2, 6-dichloropyrazine (11.0 g, 73.8 mmol) and formamide (58.6 mL, 1, 476 mmol) was added dropwise sodium persulfate (17.1 g, 71.7 mmol). The reaction mixture was stirred at 90 for 2 h and was further stirred at rt for 12 h. After dilution with water, the mixture was extracted with isopropanol/chloroform (1/3) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (70percent n-hexane/EtOAc) to afford 3, 5-dichloropyrazin-2-carboxamide (5.06 g, 36percent) as an oil.107241 2, 6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heatedto 90 °C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90 °C in portions (1 g)20-3 0 second intervals. An exotherm was observed and the color of the mixture turned from yellowto dark red/brown. The mixture was stirred at 90 °C for 2 h and then cooled to room temperature.The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. Theaqueous layer was extracted with IPAchloroform (1/3, 3 x 750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent EtOAc in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield). ‘HNMR (400 IVIHz, DMSO-d6): ppm 8.87 (s, 1H), 8.18 (br. s., 1H), 8.01 (br. s., 1H).2, 6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heated to 90° C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90° C. in Ig portions at 20-30 seconds intervals. To a mixture of 2, 6-dichloropyrazine (11.0 g, 73.8 mmol) and formamide (58.6 mL, 1, 476 mmol) was added dropwise sodium persulfate (17.1 g, 71.7 mmol). The reaction mixture was stirred at 90 for 2 h and was further stirred at rt for 12 h. After dilution with water, the mixture was extracted with isopropanol/chloroform (1/3) and washed with brine. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by column chromatography (70percent n-hexane/EtOAc) to afford 3, 5-dichloropyrazin-2-carboxamide (5.06 g, 36percent) as an oil.107241 2, 6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heatedto 90 °C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90 °C in portions (1 g)20-3 0 second intervals. An exotherm was observed and the color of the mixture turned from yellowto dark red/brown. The mixture was stirred at 90 °C for 2 h and then cooled to room temperature.The mixture was diluted with water (500 mL) and filtered. The filtrate layers were separated. Theaqueous layer was extracted with IPAchloroform (1/3, 3 x 750 mL). The combined organic layers were dried over sodium sulfate and concentrated under vacuum to afford a viscous oil. The oil was purified by silica gel chromatography (0 to 100percent EtOAc in hexanes) to provide the title product as a colorless solid (25 g, 36percent yield). ‘HNMR (400 IVIHz, DMSO-d6): ppm 8.87 (s, 1H), 8.18 (br. s., 1H), 8.01 (br. s., 1H).2, 6-Dichloropyrazine (55 g, 0.37 mol) and formamide (300 mL) were combined and heated to 90° C. Sodium persulfate (86.7 g, 0.36 mol) was added to the mixture at 90° C. in Ig portions at 20-30 seconds intervals.

Molecular Weight:192.00
XLogP3:0.9
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:190.9653171
Monoisotopic Mass:190.9653171
Topological Polar Surface Area:68.9
Heavy Atom Count:11
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes