2-AMINO-3-BROMO-5-CHLOROPYRAZINE Chemical Properties

Boiling point:

298.4±35.0 °C(Predicted)

Density 

1.96

refractive index 

1.66

storage temp. 

under inert gas (nitrogen or Argon) at 2–8 °C

pka

0.89±0.10(Predicted)

Appearance

Light yellow to brown Solid

InChI

InChI=1S/C4H3BrClN3/c5-3-4(7)8-1-2(6)9-3/h1H,(H2,7,8)

InChIKey

ACFBUXHJONGLLF-UHFFFAOYSA-N

SMILES

C1(N)=NC=C(Cl)N=C1Br

2-AMINO-3-BROMO-5-CHLOROPYRAZINE Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-3-bromo-5-chloropyrazine from 2-amino-5-chloropyrazine: 2-amino-5-chloropyrazine (3 g, 23 mmol), N-bromosuccinimide (4 g, 23 mmol), and dichloromethane (100 mL) were added to a 250 mL round-bottomed flask under nitrogen protection. The reaction mixture was heated and refluxed for 1 h before being cooled to room temperature and concentrated under reduced pressure. The crude product was purified by fast column chromatography using pentane/ethyl acetate (0 to 50%) as eluent to afford 2-amino-3-bromo-5-chloropyrazine (3 g, 62% yield).1H NMR (DMSO-d6) δ 6.8-6.9 (2H, broad single peak), 8.0 (1H, single peak). Mass spectrum (ES+): m/z 210, 212.

References

[1] Journal of Medicinal Chemistry, 1997, vol. 40, # 6, p. 996 - 1004
[2] Patent: WO2006/58074, 2006, A1. Location in patent: Page/Page column 20
[3] Patent: US5866568, 1999, A
[4] Patent: US5668137, 1997, A
[5] Patent: WO2018/98499, 2018, A1. Location in patent: Page/Page column 283