2-AMINOL-3-BENZYLOXYPYRAZINE Chemical Properties

storage temp. 

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

form 

Solid

2-AMINOL-3-BENZYLOXYPYRAZINE Usage And Synthesis

Synthesis

Benzyl alcohol (4.55 g, 42.15 mmol) was slowly added dropwise to a suspension of sodium hydride (1.01 g, 42.13 mmol, 80% dispersed in mineral oil) in N-methylpyrrolidone under inert atmosphere. The reaction mixture was stirred continuously for 30 minutes. Subsequently, 2-amino-3-chloropyrazine (5.0 g, 38.6 mmol) was added in batches and the reaction system was warmed up to 80°C maintained for 24 hours. After completion of the reaction, it was cooled to room temperature and the reaction was quenched by the addition of water (200 mL). The aqueous phase was extracted with ethyl acetate (2 x 40 mL), the organic phases were combined and washed with water (2 x 100 mL), dried over anhydrous magnesium sulfate and concentrated under reduced pressure to give a light brown solid. Crystallization was induced by adding cold water to the solid, the crystals were collected by filtration and dried with phosphorus pentoxide (6.33 g, 82% yield). The product was characterized by 1H-NMR (CDCl3): δ 7.74 (d, J=3.1 Hz, 1H), 7.45-7.32 (m, 6H), 5.38 (s, 2H), 4.78 (br s, 2H); mass spectrometry (ESI) showed the molecular ion peak m/z 202.2 ([M+H]+).

References

[1] Patent: WO2005/34837, 2005, A2. Location in patent: Page/Page column 43-44
[2] Patent: WO2005/34837, 2005, A2. Location in patent: Page/Page column 43-44
[3] Patent: KR101481952, 2015, B1. Location in patent: Paragraph 0797; 0798
[4] European Journal of Medicinal Chemistry, 2018, vol. 144, p. 529 - 543
[5] Journal of Heterocyclic Chemistry, 1990, vol. 27, # 6, p. 1639 - 1643

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