8-Chloro-imidazo[1,2-a]pyrazine Chemical Properties

Density 

1.51±0.1 g/cm3(Predicted)

storage temp. 

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

pka

1.50±0.30(Predicted)

Appearance

White to off-white Solid

InChI

InChI=1S/C6H4ClN3/c7-5-6-9-2-4-10(6)3-1-8-5/h1-4H

InChIKey

PREWHWRWNMLCNH-UHFFFAOYSA-N

SMILES

C12=NC=CN1C=CN=C2Cl

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

8-Chloro-imidazo[1,2-a]pyrazine Usage And Synthesis

Uses

8-Chloroimidazo[1,2-a]pyrazine is a useful research chemical.

Synthesis

GENERAL STEPS: Mix 48% aqueous hydrogen bromide solution (0.893 mL) with distilled water (9 mL) and add 2-bromo-1,1-diethoxyethane (5.98 mL, 38.5 mmol). It was heated and stirred under reflux conditions for 1 hour. After completion of the reaction, distilled water and ether were added to the reaction mixture for partitioning. The aqueous phase was extracted with ether, all organic phases were combined, dried with anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was mixed with a solution of 3-chloropyrazin-2-amine (2.0 g, 15.4 mmol) in dimethoxyethane (22 mL) and 48% aqueous hydrogen bromide (0.3 mL) was added. It was heated and stirred under reflux conditions for 3 hours. At the end of the reaction, the solid product was collected by filtration and washed with ether to afford 8-chloroimidazo[1,2-a]pyrazine (2.07 g, 88% yield) as a black solid. Mass spectrum (ESI) m/z = 154 ([M + H]+).

References

[1] Patent: US2012/59162, 2012, A1. Location in patent: Page/Page column 38-39
[2] Patent: WO2010/69684, 2010, A1. Location in patent: Page/Page column 96
[3] Patent: WO2011/110545, 2011, A1. Location in patent: Page/Page column 73
[4] Patent: US2012/329792, 2012, A1. Location in patent: Page/Page column 33
[5] Patent: WO2009/12482, 2009, A2. Location in patent: Page/Page column 90

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