2-Amino-5-bromo-3-ethynylpyrazine

Step 2: 5-Bromo-3-ethynyl-pyrazi n-2-ylamine To a 150 mL round-bottomed flask was added 5-bromo-3-((trimethylsilyl)ethynyl) pyrazin-2-amine (2.5 g, 9.25 mmol) and K2003 (1.279 g, 9.25 mmol) in MeOH (40 ml) to give a brownsolution. The reaction was stirred at room temp for 30 mins. The reaction was extracted into DCM, washed with water, brine, the organic layer separated, dried over MgSO4, filtered and the solvent removed under reduced pressure to yield the product as a brown solid (1.54g). LCMS; Rt 0.78 mins MS mlz 200.2. [M+H]+; Method 2minLowpH1H NMR (400MHz, DMSO-d6) O 8.12 (1H, 5), 6.86 (2H, broad 5), 4.81 (1H, 5).Step 3: 5-Bromo-3-(1 H-[1 , 2, 3]triazol-4-yl)-pyrazin-2-ylamine To a 100 mL round-bottomed flask was added 5-bromo-3-ethynylpyrazin-2-amine(800 mg, 4.04 mmol), Sodium ascorbate (0.404 ml, 0.404 mmol), and copper(ll) sulfatepentahydrate (10.09 mg, 0.040 mmol) in tertiary butanol (10.00 ml) and water (20m1) to givea brown suspension. To this was added trimethylsilyl azide (1.61m1, 12.l2mmol) and thereaction heated at 90C for 4 hours. The reaction was extracted into ethyl acetate, washed with brine, the organic layer separated, dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue was loaded onto silica and purified by flash column chromatography, elution with iso hexane:ethyl acetate (0-70%) on a 40g silca cartridge. Therequired fractions were combined and the solvent removed under reduced pressure to yieldthe product as a dark yellow solid (560mg, 57 %).LCMS: Rt 0.82 mins MS mlz 243.2. [M+H]+; Method 2minLowpH1H NMR (400MHz, DMSO-d6) O (ppm) 15.66 (1H brs), 8.52 (1H, brs), 8.14 (1H, 5), 7.46(2H, brs).Step 2: 5-Bromo-3-ethynyl-pyrazi n-2-ylamine To a 150 mL round-bottomed flask was added 5-bromo-3-((trimethylsilyl)ethynyl) pyrazin-2-amine (2.5 g, 9.25 mmol) and K2003 (1.279 g, 9.25 mmol) in MeOH (40 ml) to give a brownsolution. The reaction was stirred at room temp for 30 mins. The reaction was extracted into DCM, washed with water, brine, the organic layer separated, dried over MgSO4, filtered and the solvent removed under reduced pressure to yield the product as a brown solid (1.54g). LCMS; Rt 0.78 mins MS mlz 200.2. [M+H]+; Method 2minLowpH1H NMR (400MHz, DMSO-d6) O 8.12 (1H, 5), 6.86 (2H, broad 5), 4.81 (1H, 5).

Molecular Weight:198.02
XLogP3:0.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:51.8
Heavy Atom Count:10
Complexity:162
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes