Diaminomethyleneaminocarbonyldinitromethane, formed during the preparationof 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone by nitration of 2-amino-6-chloro-4(3H)-pyrimidinone

Authors
Boyle, PH Daly, KM Leurquin, F Robinson, JK Scully, DT
Citation
Ph. Boyle et al., Diaminomethyleneaminocarbonyldinitromethane, formed during the preparationof 2-amino-6-chloro-5-nitro-4(3H)-pyrimidinone by nitration of 2-amino-6-chloro-4(3H)-pyrimidinone, TETRAHEDR L, 42(9), 2001, pp. 1793-1795
Citations number
11
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON LETTERS
ISSN journal
00404039 → ACNP
Volume
42
Issue
9
Year of publication
2001
Pages
1793 - 1795
Database
ISI
SICI code
0040-4039(20010226)42:9<1793:DFDTP>2.0.ZU;2-Y
Abstract
Difficulties in the nitration of 2-amino-6-chloro-4(3H)-pyrimidinone to giv e the widely used heterocyclic precursor 2-amino-6-chloro-5-nitro-4(3H)-pyr imidinone are shown to be due to formation of an unusual open-chain gem-din itro compound, identified as diaminomethyleneaminocarbonyldinitromethane. T he latter is also formed by the nitration of 2-amino-4,6(3H,5H)-pyrimidined ione. It decomposes with loss of carbon dioxide in dimethyl sulfoxide, or i n aqueous potassium hydroxide, to give guanidine and dinitromethane. (C) 20 01 Elsevier Science Ltd. All rights reserved.