isopropanol, ethanol failed to react at position five of 5-bromo-2,3-disubsttiued pyrazine at position 2, there is ethanolamine and at position 3, there is chlorine atom .
does it relay to orientation of isopropanol and ethanol?! or acidity impact in SNAr mechanism ?!
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James Demers
The pyrazine is deactivated by the amino substituent, and an SnAr reaction just isn't going to happen. With a BOC-protected amino group, and a stronger base (t-butoxide) you might see a benzyne-type of mechanism, with a mixture of 5- and 6-alkoxy products.
You might have more luck acetylating the 5-position, then doing a Baeyer–Villiger oxidation.
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Laurance Bourghli
Can you write the IUPAC name of your starting material or sketch a drawing for it? what conditions did you use?
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