June 02, 2020, 12:04:55 PM
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Topic: Mechanism for replacement of SCH3 by OH using 2-mercaptoethanol?  (Read 147 times)

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Offline GinaTageldin

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i have 4-aryl-1-methyl-2-methylsulfanyl-6-oxo-1,6-dihydropyrimidine-5-carbonitrile derivative
and i reacted it with 2-mercaptoethanol in dichloromethane and DIPEA at room temperature for 14 h, the resulted product revealed removal of the methylsulfanyl moiety and introduction of a OH group?
Also i reacted the same compound with oxone and yielded the same product? Any explanation for the mechanism using 2-mercaptoethanol

Offline pgk

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Re: Mechanism for replacement of SCH3 by OH using 2-mercaptoethanol?
« Reply #1 on: March 18, 2020, 01:52:31 PM »
Think about a DIPEA catalyzed, thiirane formation that liberates a hydroxyl anion, which attacks to the 2 position and liberates the methylsulfanyl group. The transition intermediate is stabilized by conjugation with the nitrile group, through the unsaturated ring.

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