Molbank 2005, M431

http://www.mdpi.net/molbank/

5-Methoxy-1,3-dimethyl-1H-pyrazolo[4,3-e][1,2,4]triazine

Mariusz Mojzych^* and Danuta Branowska

Institute of Chemistry, University of Podlasie,

ul. 3 Maja 54, 08-110 Siedlce, Poland

e-mail: [email protected]

Received: 23 April 2004 / Accepted: 7 June 2004 / Published: 1 October 2005

Keywords: fluviols, nucleophilic substitution.

O- and N-alkyl derivatives of pyrazolo[4,3-e][1,2,4]triazine, isolated from the cultural fluids of Pseudomonas fluorescens and Nostoc spongiaeforme exhibit antimicrobial and antitumor activity [1-2]. In this communication we report the synthesis of 5-methoxy-1,3-dimethyl-1H-pyrazolo[4,3-e][1,2,4]triazine (2) with the goal of performing structure-activity relationship studies.

To a solution of the sulfone 1 (145 mg, 0.5 mmol) in absolute methanol (10 ml) metal sodium (35 mg, 1.5 mmol) was added. The reaction mixture was heated at reflux for 30 min. After usual work-up compound 2 was purified by column chromatography (Merck, silica gel 230-400 mesh) using CHCl₃ as eluent. The 1,3-dimethyl-5-methoxy-1H-pyrazolo[4,3-e][1,2,4]triazine (2) was isolated in 96% yield.

Melting Point: 110^ºC.

¹H-NMR (200 MHz, CDCl₃): δ= 2.59 (s, 3H); 4.20 (s, 3H); 4.24 (s, 3H).

IR (KBr, cm^-1): 2960; 1310; 1120; 1050.

MS- EI (m/z): 179[M⁺].

Elemental Analysis: Calculated for C₇H₉N₅O: C, 46.93%; H, 5.02%; N, 39.10%. Found: C, 47.20%; H, 4.94%; N, 38.89%.

References:

1.Smirnov, V.V.; Kiprianowa, E.A.; Garagulya, A.D.; Esipov, S. E.; Dovjenko, S. A., FEMS Microbiology Lett., 1997, 153, 357.

2.Hirata, K.; Nakagami, H.; Takashina, J.; Mahmud, T.; Kobayashi, M.; In, Y.; Ishida, T.; Miyamoto, K., Heterocycles, 1996, 43, 1513.

Sample Availability: Available from MDPI.

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