Abstract
A robust synthesis of Soai-type pyrimidine aldehydes proceeds in good to high yields by controlled formation and quenching of a lithiated pyrimidine intermediate. The alkyne-substituted bromopyrimidine, furnished by Sonogashira cross-coupling, underwent a Barbier-type halogen-lithium exchange to form a transient pyrimidinyl lithium species. The rate of n-BuLi addition was optimized to better synchronize with the addition to ethyl formate, in order to achieve consistently high yields of 2-alkylpyrimdinecarboxaldehydes for use in autocatalysis or as functionalized synthons.
| Original language | English |
|---|---|
| Article number | e202100787 |
| Pages (from-to) | 1-6 |
| Number of pages | 6 |
| Journal | Asian Journal of Organic Chemistry |
| Volume | 11 |
| Issue number | 7 |
| Early online date | 27 Jan 2022 |
| DOIs | |
| Publication status | Published - Jul 2022 |
Bibliographical note
Copyright the Author(s) 2022. Version archived for private and non-commercial use with the permission of the author/s and according to publisher conditions. For further rights please contact the publisher.Keywords
- asymmetric autocatalysis
- barbier-type lithiation
- metalated pyrimidines
- pyrimidine carboxaldehyde preparation
- transient intermediate capturing