Next Article in Journal
1-[4-[Bis(2-chloroethyl)amino]benzyl]-5,5-dimethyl-2,5-dihydro-4H-benzo[e]isoindol-4-one (Cytotoxic Oxonaphthalene-pyrroles, Part II)
Previous Article in Journal
6-Oxo-3-phenyl-5,6-dihydropyridazine-1(4H)-carbohydrazide
 
 
Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
Journals
Molbank
Volume 2010
Issue 1
10.3390/M653
molbank-logo
Submit to this Journal Review for this Journal Propose a Special Issue
► Article Menu

Article Menu

share Share announcement Help format_quote Cite question_answer Discuss in SciProfiles thumb_up
...
Endorse textsms
...
Comment
first_page
settings
Order Article Reprints
Font Type:
Arial Georgia Verdana
Font Size:
Aa Aa Aa
Line Spacing:
Column Width:
Background:
Short Note

4,6-Diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one

by
Gricela Lobo
1,*,
Jaime Charris
1,
Margaret Valderrama
1,
Jesús Romero
1,
Cristina Castelli
2 and
Antonieta Taddei
2
1
Laboratorio de Síntesis Orgánica, Facultad de Farmacia, Universidad Central de Venezuela, Caracas 1051, Venezuela
2
Departamento de Biología Celular, Universidad Simón Bolívar, Caracas 1080, Venezuela
*
Author to whom correspondence should be addressed.
Molbank 2010, 2010(1), M653; https://doi.org/10.3390/M653
Submission received: 26 November 2009 / Accepted: 11 December 2009 / Published: 27 January 2010
Versions Notes

Abstract

:
A new compound, 4,6-diamino-5-(methylbenzylidene)pyrimidin-2(5H)-one, was synthesized and its IR, 1H NMR,13C NMR and MS spectroscopic data are presented.

Pyrimidines and their derivatives are considered an important group of compounds because of the diversity of biological activities associated with these systems. Among the activities reported for pyrimidines have been found antifolate [1], antimicrobial [2], leishmanicidal [3], anticonvulsant [4], anti-rubella [5], anti-HIV [6], calcium channel modulation [7], and selective hepatitis B virus inhibition [8].
In the specialized literature, we can find different articles on the synthesis of substituted pyrimidines and many detailed reviews have appeared [9,10,11,12]. Recently, the Biginelli reaction is a well-known multicomponent reaction involving a one-pot cyclocondensation of an aldehyde, a methylene active compound and urea/thiourea for the synthesis of pyrimidine derivatives [13,14,15]. Nevertheless, little attention is given to the synthesis and biological activity of the pyrimidine nucleus having the benzylidene group in position 5, close to amino groups at positions 4 and 6. We report here the synthesis and biological activity of 4,6-diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one 2.
Molbank 2010 m653 i001
A mixture of (4-methylbenzilidene)malononitrile 1 [16,17,18] (0.2 g, 1.19 mmol), urea (0.14 g, 2.33 mmol), and K2CO3 (0.20 g, 1.17 mmol) in methanol was refluxed for 24 h. The reaction mixture was neutralized with HCl (10% v/v). The solid was filtered and washed with water. After recrystallization using methanol, 4,6-diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one 2 was obtained as a brown solid (0.18 g, 80%). Synthesis of other pyrimidine derivatives and studies of their biological activities are in progress, mainly tests of antimicrobial activity as a part of a research program directed to the synthesis of novel heterocyclic compounds of pharmacological interest.
M.p.: 172–175 ºC.
IR (KBr, cm-1): 3271 (NH2), 1780 (C=O), 1651 (C=N).
1H NMR (CDCl3, 270 MHz): δ: 8.34 (1H, s, olefinic-H); 7.89 (2H, dd, J = 8.9, 2.0 Hz, Ar-H); 7.18 (2H, dd, J = 8.9, 2.0 Hz, Ar-H); 4.91 (4H, br, NH2); 2.30 (3H, s, CH3).
13C NMR (CDCl3, 69 MHz): δ: 160.02; 156.61; 144.07; 139.07; 132.28; 130.89; 129.02; 128.16; 21.17.
EI, MS (m/z, %): 228 (M+, 29%); 213 (M+ - CH3); 168 (M+ - CO-N2H4, 100%).
Anal. Calcd for C12H12N4O: C, 63.07%; H, 5.26%; N, 24.53%. Found: C, 63.47%; H, 5.41%;
N 24.87%.
Biological Activity: Compound 2 showed antimicrobial activity against Escherichia coli (ATCC 35218) (ATCC 25922) (gram negative bacteria).

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

Acknowledgements

We are grateful to “Consejo de Desarrollo Científico y Humanístico de la Universidad Central de Venezuela /CDCH-UCV)” for financing the Project: PI 06-00-6759-2007.

References and Notes

  1. Prabakaran, P.; Robert, J.J.; Muthiah, P.T.; Bocelli, G.; Righi, L. Aminopyrimidine-carboxylate interactions in trimethoprim maleate, an antifolate drug. Acta Crystallogr. C. 2001, 57, 459–461. [Google Scholar] [CrossRef] [PubMed]
  2. Gössnitzer, E.; Feierl, G.; Wagner, U. Synthesis, structure investigations, and antimicrobial activity of selected s-tran-6-aril-4-isopropyl-2-2[2-[(E)-1-phenylalkylidene]-(E)-hydrazino]-1,4-dihydropyrimidine hydrochlorides. Eur. J. Pharm. Sci. 2002, 15, 49–61. [Google Scholar] [CrossRef]
  3. Ram, V.J.; Haque, N. Synthesis of functionalized pyrazolo [3,4-d] pyrimidine as potential leishmanicides. Indian J. Chem. 1995, 34B, 521–524. [Google Scholar]
  4. Calis, U.; Koksal, M. Synthesis and evaluation of anticonvulsant activities of some new aryl-hexahypyrimidines-2,4-diones. Arzneimittelforschung 2001, 51, 523–528. [Google Scholar] [PubMed]
  5. Saladino, R.; Ciambecchini, U.; Maga, G.; Mastromarino, P.; Conti, C.; Botta, M. A new and efficient synthesis of substituted 6-[(2’-dialkylamino) ethyl] pyrimidine and 4, N,N-dialkyl-6-vinylcytosine derivatives and evaluation of their anti-Rubella activity. Bioorg. Med. Chem. 2002, 2143–2153. [Google Scholar] [CrossRef]
  6. San-Felix, A.; Velazquez, S.; Perez-Perez, M.J.; Balzarini, J.; De Clercq, E.; Canarasa, M.J. Novel series of TSAO-T derivatives. Synthesis and anti-HIV-1 activity of 4-, 5-. and 6- substituted pyrimidine analogues. J. Med. Chem. 1994, 37, 453–460. [Google Scholar] [CrossRef] [PubMed]
  7. Vanden, J.; Audiart, N.; Canonne, V.; Michel, S.; Van Haverbeke, Y.V.; Kappe, C. Synthesis and reactions of Biginelli compunds, 10. Synthesis and aromatization of dihydropyrimidines structurally related to calcium channel modulators of the Nifedipine-type. Heterocycles 1997, 45, 1967–1978. [Google Scholar]
  8. Kumar, R.; Nath, M.; Tyrrell, D.J. Design and synthesis of novel 5-substituted acyclic pyrimidine nucleosides as potent and selective inhibitor of hepatitis B virus. J. Med. Chem. 2002, 45, 2032–2040. [Google Scholar] [CrossRef] [PubMed]
  9. Kenner, G. W.; Todd, A. Heterocyclic Compounds; Elderfiel, R.C., Ed.; Wiley: New York, NY, USA, 1957; Vol. 6. [Google Scholar]
  10. Brow, D.J. The Chemistry of Heterocyclic Compounds; Weissberger, A., Ed.; Interscience: New York, NY, USA, 1962; Vol. 16. [Google Scholar]
  11. Yildirin, I.; Akcamur, Y.; Saripinar, E.; Kollenz, G. On the synthesis of some derivatives and determination of their structures. Kuwait J. Sci. Eng. 2002, 29, 57–65. [Google Scholar]
  12. Abdel-Razik, H.H.; Said, S.B. Enaminonitrile in Heterocyclic Synthesis: Synthesis and reactions of some pyrimidine derivatives. Chem. Pap. 2004, 58, 209–213. [Google Scholar]
  13. Lu, J.; Bai, Y. Catalysis of the Biginelli Reaction by Ferric and Nickel Chloride Hexahydrates. One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones. Synthesis 2002, 466–470. [Google Scholar] [CrossRef]
  14. Hazarkhani, H.; Karimi, B. N-Bromosuccinimide as an Almost Neutral Catalyst for Efficient Synthesis of Dihydropyrimidinones Under Microwave Irradiation. Synthesis 2004, 1239–1242. [Google Scholar]
  15. Aydin, F. Synthesis of 4-[4-(dimethylamino)phenyl)]-5-acethyl-6-phenyl-3,4-dihydropyrimidin-2-(1H)thione. Molbank 2006, M468. [Google Scholar] [CrossRef]
  16. Tietze, I. F.; Beifus, U.; Trost, B.; Fleming, I.; Heathcock, C.H. Comprehensive Organic Synthesis; Pergamon Press: Oxford, UK, 1991; Vol. 2, Chapter 1.11; p. 341. [Google Scholar]
  17. Jones, G. Organic Reaction; Wiley: New York, NY, USA, 1967; Vol. 15, p. 204. [Google Scholar]
  18. Laulan, A.; Sauger, A.; Germain, C.; Montembault, A.-M.; Sans, I.; Potentini-Esnault, C.; Chicane, L.; Gilard, C.; Sultan, Y.; Bartholeyns, J.; Binev, I.G.; Binev, Y.I.; Stamboliyska, B.A.; Juchnovski, I.N. IR spectra and structure of benzylidenemalononitrile and its cyanide, methoxide and heptylamine adducts: experimental and ab initio studies. J. Mol. Struct. 1997, 435, 235–245. [Google Scholar]

Share and Cite

MDPI and ACS Style

Lobo, G.; Charris, J.; Valderrama, M.; Romero, J.; Castelli, C.; Taddei, A. 4,6-Diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one. Molbank 2010, 2010, M653. https://doi.org/10.3390/M653

AMA Style

Lobo G, Charris J, Valderrama M, Romero J, Castelli C, Taddei A. 4,6-Diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one. Molbank. 2010; 2010(1):M653. https://doi.org/10.3390/M653

Chicago/Turabian Style

Lobo, Gricela, Jaime Charris, Margaret Valderrama, Jesús Romero, Cristina Castelli, and Antonieta Taddei. 2010. "4,6-Diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one" Molbank 2010, no. 1: M653. https://doi.org/10.3390/M653

APA Style

Lobo, G., Charris, J., Valderrama, M., Romero, J., Castelli, C., & Taddei, A. (2010). 4,6-Diamino-5-(4-methylbenzylidene)pyrimidin-2(5H)-one. Molbank, 2010(1), M653. https://doi.org/10.3390/M653

Note that from the first issue of 2016, this journal uses article numbers instead of page numbers. See further details here.

Article Metrics

Back to TopTop