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Heterocyclic Communications

Editor-in-Chief: Strekowski, Lucjan

Ed. by Baumstark, Alfons L. / Saczewski, Jaroslaw / Stephens, Chad / Yamada, Hidetoshi

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2191-0197
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Volume 21, Issue 6 (Dec 2015)

Issues

Synthesis of 2-amino-6,7,8,9-tetrahydro-6-phenethyl-3H-pyrimido[4,5-e][1,4]diazepin-4(5H)-one: a model for a potential pyrimido[4,5-e][1,4]diazepine-based folate anti-tumor agent

Austin W. Gann / Partha S. Ray
Published Online: 2015-11-26 | DOI: https://doi.org/10.1515/hc-2015-0216

Abstract

Reductive cyclization of 2-{N-[(2-amino-4,6-dichloropyrimidin-5-yl)methyl]-N-phenethylamino}acetonitrile (5) with Raney nickel and hydrogen gave the chloropyrimido[4,5-e][1,4]diazepine 3 which could not be converted to 2 via an attempted nucleophilic aromatic substitution with hydroxide. The title compound (2) was prepared, however, by the reductive cyclization of 2-{N-[(2-amino-4-chloro-6-methoxypyrimidin-5-yl)methyl]-N-phenethylamino}acetonitrile (13) followed by treatment with trimethyliodosilane.

Keywords: pyrimidodiazepine; pyrimido[4,5-e][1,4]diazepine; reductive cyclization

Dedicated with admiration and affection to the memory of my (PSR) undergraduate and graduate mentor Professor Sandy McKillop.

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About the article

Corresponding author: Partha S. Ray, Department of Chemistry, University of West Georgia, Carrollton, GA 30118, USA, e-mail:


Received: 2015-09-24

Accepted: 2015-11-04

Published Online: 2015-11-26

Published in Print: 2015-12-01


Citation Information: Heterocyclic Communications, ISSN (Online) 2191-0197, ISSN (Print) 0793-0283, DOI: https://doi.org/10.1515/hc-2015-0216.

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