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

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 Information

HS Code 

2933998090

3-Amino-6-bromopyrazine-2-carboxylic acid Usage And Synthesis

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

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