3,5-DIBROMO-N,N-DIMETHYLPYRAZINAMINE Chemical Properties

Melting point:

80-81 °C

Boiling point:

300.0±40.0 °C(Predicted)

Density 

1.921±0.06 g/cm3(Predicted)

storage temp. 

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

pka

0.89±0.10(Predicted)

3,5-DIBROMO-N,N-DIMETHYLPYRAZINAMINE Usage And Synthesis

Synthesis

To a stirred solution of 2-amino-3,5-dibromopyrazine (1.0 mmol) in anhydrous DMF (3 mL) was added sodium hydride (60% dispersion in mineral oil, 2.2 mmol) and iodomethane (4.0 mmol). The reaction mixture was stirred for 25 min at room temperature under nitrogen protection. After completion of the reaction, the reaction was quenched with water (6 mL) and extracted with ether (2 x 12 mL). The organic phases were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated to give the crude product. Purification by column chromatography (12 g ISCO column, eluent gradient of 100% hexane to 70% hexane with ethyl acetate) afforded 3,5-dibromo-N,N-dimethylaminopyrazine (171 mg, 61% yield) as a yellow oil.1H NMR (300 MHz, CDCl3) δ 8.11 (s, 1H), 3.07 (s, 6H).

References

[1] Bioorganic and Medicinal Chemistry, 2001, vol. 9, # 5, p. 1149 - 1154
[2] Patent: US2006/142307, 2006, A1. Location in patent: Page/Page column 4-5; 19

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