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

Author:

Gann Austin W.1,Ray Partha S.1

Affiliation:

1. 1Department of Chemistry, University of West Georgia, Carrollton, GA 30118, USA

Abstract

AbstractReductive 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.

Publisher

Walter de Gruyter GmbH

Subject

Organic Chemistry

Reference18 articles.

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2. Synthesis of amino chloro bis dimethoxybenzyl tetrahydro pyrimido diazepine a potentially useful intermediate to pyrimido diazepine - based folates Heterocycl;Huddleston,2004

3. Structural features of dideaza - tetrahydrofolate that determine inhibition of mammalian glycinamide ribonucleotide formyltransferase;Baldwin;Biochemistry,1991

4. Synthesis ofN amino oxo tetrahydro pyrimido azepin yl benzoyl glutamic acid and two of its conformationally - restricted analogs;Read;Tetrahedron,1999

5. Cyanomethylation with chloroacetonitrile;Sidhu;J Chem,1964

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