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Volume 2010
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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

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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

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