On the N‐ethylation of 4‐alkoxy‐ and 4,6‐dialkoxypyrimidines with triethyloxonium tetrafluoroborate
- 1 January 1977
- journal article
- research article
- Published by Wiley in Recueil des Travaux Chimiques des Pays-Bas
- Vol. 96 (3) , 64-68
- https://doi.org/10.1002/recl.19770960303
Abstract
Reaction of 4‐alkoxy‐(1–4) or 4,6‐dialkoxypyrimidines (5–9) with 1 equivalent of triethyloxonium tetrafluoroborate yields 4‐alkoxy‐N‐ethyl (13–15) or 4,6‐dialkoxy‐N‐ethylpyrimidinium salts (10–12), respectively. With two or more equivalents of this reagent, rearrangement of N‐ethylalkoxypyrimidinium salts into 1‐ethyl‐3‐alkyl‐1,4(3,4)‐dihydro‐4‐oxopyrimidinium salts (16–22) takes place. These rearrangements can also be performed by heating. The mechanism of these rearrangement reactions is discussed.Funding Information
- Netherlands Organisation for the Advancement of Pure Research
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