4.6 Article

Regioselective N-alkylation with alcohols for the preparation of 2-(N-alkylamino)quinazolines and 2-(N-alkylamino)pyrimidines

Journal

NEW JOURNAL OF CHEMISTRY
Volume 37, Issue 3, Pages 624-631

Publisher

ROYAL SOC CHEMISTRY
DOI: 10.1039/c2nj41021d

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Funding

  1. National Natural Science Foundation of China [21272115]
  2. Natural Science Foundation of Jiangsu Province [BK2009384]
  3. Fundamental Research Funds for the Central Universities [NUST2011ZDJH19]

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In the presence of the [Cp*IrCl2](2)/NaOH system, the direct N-alkylation of 2-aminoquinazolines and 2-aminopyrimidines with alcohols afforded the N-exosubstituted 2-(N-alkylamino)quinazolines and 2-(N-alkylamino)pyrimidines with 71-96% yields and complete regioselectivities. The protocol is highly attractive because of easily available starting materials, high atom efficiency and environmental friendliness.

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