2-Amino-3-bromo-5-methylpyrazine Chemical Properties

Melting point:

56-57 °C

Boiling point:

275.0±35.0 °C(Predicted)

Density 

1.699±0.06 g/cm3(Predicted)

storage temp. 

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

pka

2.65±0.10(Predicted)

Appearance

Off-white to light yellow Solid

Safety Information

HazardClass 

IRRITANT

HS Code 

2933998090

2-Amino-3-bromo-5-methylpyrazine Usage And Synthesis

Synthesis

General procedure for the synthesis of 2-amino-3-bromo-5-methylpyrazine from 2-amino-5-methylpyrazine: Bromine (8.80 g, 55.0 mmol) was slowly added to a solution of dichloromethane (250 mL) containing 5-methylpyrazin-2-amine (5.00 g, 45.8 mmol) and pyridine (4.35 g, 55.0 mmol). The reaction mixture was stirred overnight at room temperature. Upon completion of the reaction, water (150 mL) was added to the mixture for extraction and the organic layer was separated. The organic layer was washed with saturated brine (100 mL), dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under vacuum to afford the target compound 2-amino-3-bromo-5-methylpyrazine as a yellow solid (7.64 g, 88% yield). Mass spectrum (ESI, positive ion mode) m/z: 190.2 [M + H]+; 1H NMR (400 MHz, CDCl3) δ (ppm): 7.83 (s, 1H), 4.93 (s, 2H), 2.41 (s, 3H).

References

[1] Patent: WO2018/108125, 2018, A1. Location in patent: Paragraph 00511
[2] Patent: WO2018/136265, 2018, A1. Location in patent: Paragraph 00790
[3] Patent: US2014/275531, 2014, A1. Location in patent: Paragraph 0353
[4] Patent: JP5714745, 2015, B2. Location in patent: Paragraph 0687; 0688
[5] Patent: US5866568, 1999, A

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