3-Amino-6-bromopyrazine-2-carboxylic acid

3-Amino-6-bromopyrazine-2-carboxylic acid Property

Melting point:

178-183℃

Boiling point:

397.8±42.0 °C(Predicted)

Density 

2.039±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Inert atmosphere,Store in freezer, under -20°C

solubility 

Soluble in dimethyl sulfoxide and methanol.

pka

3.26±0.10(Predicted)

form 

Solid

color 

Pale yellow

Sensitive 

Light Sensitive

InChI

InChI=1S/C5H4BrN3O2/c6-2-1-8-4(7)3(9-2)5(10)11/h1H,(H2,7,8)(H,10,11)

InChIKey

MTNAQEKMSVDTAQ-UHFFFAOYSA-N

SMILES

C1(C(O)=O)=NC(Br)=CN=C1N

Safety

HS Code 

2933998090

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P405Store locked up.

3-Amino-6-bromopyrazine-2-carboxylic acid Chemical Properties,Usage,Production

Chemical Properties

Yellow Solid

Uses

3-Amino-6-bromopyrazine-2-carboxylic acid used to prepare 3-bromo-5-phenylpyrazine-2-amine. It serves as an intermediate in organic synthesis and pharmaceuticals.

Synthesis

Step 2: Methyl 3-amino-6-bromopyrazine-2-carboxylate (5.11 g, 22.02 mmol) and lithium hydroxide (2.637 g, 110.1 mmol) were dissolved in a mixed solvent of methanol (20 mL) and water (20 mL), heated to 90 °C, and the reaction was carried out for 2 hours. After completion of the reaction, the reaction mixture was cooled, neutralized with hydrochloric acid to pH neutral, and the precipitated solid was collected by filtration. The resulting 3-amino-6-bromopyrazine-2-carboxylic acid was used directly in the next step of the reaction without further purification (4.80 g, 99% yield).

References

[1] Patent: WO2011/143419, 2011, A1. Location in patent: Page/Page column 44-45
[2] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 8, p. 2784 - 2788
[3] Journal of Medicinal Chemistry, 2011, vol. 54, # 7, p. 2320 - 2330
[4] Patent: WO2017/123588, 2017, A1. Location in patent: Paragraph 0031; 0032; 0033
[5] Patent: WO2010/54398, 2010, A1. Location in patent: Page/Page column 90