3-AMINO-6-BROMOPYRAZINE-2-CARBONITRILE

Step 1: synthesis of 3-amino-6-bromopyrazine-2-carbonitrile (14)A solution of copper(i) cyanide (1.20 g, 13.42 mmol) and sodium cyanide (0.658 g, 13.42 mmol) in DMF (10 mL) was heated to 125°C. 2-amino-3, 5-dibromo pyrazine (2.61 g, 10.32 mmol) was added in portions. The reaction was stirred at 125°C, and after 5h quenched in ice cold NaHC0Step 1: The suspension of 18b (2.51 g, 10.0 mmol), NaCN (0.59 g, 12.0 mmol), CuI (0.95 g, 5.0 mmol) and Pd(PPh3)4 (0.14 g, 0.1 mmol) were stirred in DMF (20 mL) at 120 C for 10 h under nitrogen protection. After cooling to room temperature, 10% aqueous solution of Na2S2O3(10 mL) and water(50 mL) were added. The mixture was extracted with ethyl acetate (50 mL × 3), washed with water (3 × 50 mL), dried over anhydrous Na2SO4 and concentrated. The residue was purified by chromatography on silica gel eluting with PE/EA (10:1-2:1) to give an off-white solid (1.1 g, yield 55%). 6-Bromo-3-aminopyrazine-2-carbonitrile (19b)Yield: 55%, off-white solid, M.p.: 180-182 C (Lit.183-184 C, Sato et al. 1990a, b). 1H NMR (400 MHz, DMSO-d6): delta 8.45 (s, 1H), 7.62 (s, 2H). 1H NMR (400 MHz, CDCl3):delta 8.30 (s, 1H), 5.28 (s, 2H). 13C NMR (125 MHz, DMSO-d6): delta 156.70, 150.49, 123.64, 115.45, 110.60. EI-MS m/z: 198 (M+, Br79, 100), 200 (M+, Br81, 98), 171(M+, Br79, -H, -CN, 17), 173 (M+, Br81, -H, -CN, 17), 119(M+, -Br, 32), 92 (M+, -Br, -H, -CN, 46).

Molecular Weight:199.01
XLogP3:1.1
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:4
Exact Mass:197.95411
Monoisotopic Mass:197.95411
Topological Polar Surface Area:75.6
Heavy Atom Count:10
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes