3-Amino-6-bromo-2-pyrazinecarboxylic acid

Yellow Solid

Step 2: 3-Amino-6-bromopyrazine-2-carboxylic acid[00140] A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (5.1 1 g, 22.02 mmol) and lithium hydroxide (2.637 g, 110.1 mmol) in MeOH (20 mL) and Ι3/40 (20 mL) was heated to 90 °C for 2 hours. The reaction mixture was allowed to cool and neutralized with HCl and the resultant precipitate collected by filtration. The sub-title product was taken on to the next step without further purification (4.80g, 99percent Yield).To the solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (10.0 g 43.1 mmol) in MeOH (70 mL) was added a solution of Li OH (9.0 g, 215 mmol) in water (70 mL). The mixture was stirred at 90 °C for 3 hours. The reaction mixture was cooled to rt and acidified to PH = 4-5 with HC1 (2 M). The mixture was filtered to afford 7.4 g of 6 (79 percent) as yellow solid. (0170) [0033] LC-MS (M+l): 218.0; 1H MR (400 MHz, DMSO-d6) δ 8.39 (s, 1H), 7.59 (br, 2H).Step 2 : 3-amino-6-bromopyrazine-2-carboxylic acid[00211] A mixture of methyl 3-amino-6-bromo-pyrazine-2-carboxylate (3 g, 12.93 mmol) and lithium hydroxide (1.548 g, 64.65 mmol) in MeOH (11.74 mL) and H2O (11.74 mL) was heated to 90 (Step 6-ii) To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (1 g, 4.33 mmol) in 10 mL THF was added a solution of LiOH (540 mg, 12.86 mmol) in 20 mL of water. The mixture was stirred at room temperature for 4 hours and acidified with 6M HCl to a pH of 2. The yellow precipitate was collected by filtration and washed with water. After drying in vacuo, the product, 3-amino-6-bromopyrazine-2-carboxylic acid (600 mg, 2.75 mmol, 64percent yield), can be used directly in the next reaction without further purification.To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43 mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at 50°C for 4 h, the mixture was cooled and acidified with 1 M HCl to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6- bromopyrazine-2-carboxylic acid (90 mg, yield: 96percent). To a solution of methyl 3-amino-6-bromopyrazine-2-carboxylate (100 mg, 0.43mmol) in MeOH (5 mL) was added 2 mL of NaOH aqueous solution (5 N). After being stirred at50°C for 4 h, the mixture was cooled and acidified with 1 M HC1 to a pH of 2. The precipitate was collected by filtration and washed with water to afford the product of 3-amino-6-bromopyrazine-2-carboxylic acid (90 mg, yield: 96percent). ‘H-NMR (DMSO-d6, 400 MHz) 8.38 (s, 1H), 7.517.56 (m, 2H). MS (M+H): 218 / 220.

Molecular Weight:218.01
XLogP3:0.9
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:1
Exact Mass:216.94869
Monoisotopic Mass:216.94869
Topological Polar Surface Area:89.1
Heavy Atom Count:11
Complexity:166
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes