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Volume 2005
Issue 2
10.3390/M415
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Short Note

Synthesis of 5-(2-aminoethoxy)-3-methyl-1-phenyl-1H-pyrazolo[4,3-E][1,2,4]triazine

by
Mariusz Mojzych
Institute of Chemistry, University of Podlasie, ul. 3 Maja 54, 08-110 Siedlce, Poland
Molbank 2005, 2005(2), M415; https://doi.org/10.3390/M415
Submission received: 23 April 2004 / Accepted: 30 July 2004 / Published: 1 August 2005
Versions Notes

A variety of naturally occurring O- and N-derivatives of 1H-pyrazolo[4,3-e][1,2,4]triazine exhibit an interesting combination of biological activity [1,2]. As a part of our ongoing research programme [3,4,5,6] we have synthesised a novel 5-(2-aminoethoxy)- 3-methyl-1-phenyl-1H-pyrazolo[4,3-E][1,2,4]triazine derivative of this ring system based on nucleophilic displacement of methylsulfonyl group [6].
Molbank 2005 m415 i001 To a solution of sulfone 1 (145 mg, 0.5 mmol) in anhydrous DMF (5 ml) 2-aminoethanol (0.5 ml) was added and the resulting mixture was stirred at 80 °C for 2 h. After pouring onto cold water the precipitate was filtered off, washed with water and recrystallized from ethyl alkohol to give 5-(2-aminoethoxy)-3-methyl-1-phenyl-1H-pyrazolo[4,3-e][1,2,4]triazine (2) in 90% yield.
Melting Point: 164 °C.
1H-NMR (200 MHz, CDCl3): δ= 2.61 (s, 3H); 3.76-3.81 (m, 2H); 3.96 (t, 2H, J=6.0 Hz); 6.10 (s, 2H); 7.29-7.33 (m, 1H); 7.48-7.56 (m, 2H); 8.26-8.31 (m, 2H).
IR (KBr, cm-1): 3243; 2948; 1580; 1540; 750; 689.
MS (EI, 70eV; m/z, %): 270 (68) [M+]; 242 (4); 211 (60); 184 (14); 131 (20); 104 (42); 77 (100).
Elemental Analysis: Calculated for C13H14N6O: C, 57.77%; H, 5.18%; N, 31.11%. Found: C, 57.67%; H, 5.17%; N, 31.16%.

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3Supplementary File 4Supplementary File 5Supplementary File 6

References

  1. Hirata, K.; Nakagami, H.; Takashina, J.; et al. Heterocycles 1996, 43, 1513.
  2. Smirnov, V.V.; Kiprianowa, E.A.; et al. FEMS Microbiology Lett. 1997, 153, 357.
  3. Rykowski, A.; Mojzych, M.; Karczmarzyk, Z. Heterocycles 2000, 53, 2175.
  4. Karczmarzyk, Z.; Mojzych, M.; Rykowski, A. J. Chem. Cryst. 2000, 30, 423.
  5. Mojzych, M.; Rykowski, A. Polish J. Chem. 2003, 77, 1797.
  6. Mojzych, M.; Rykowski, A. Heterocycles 2004. submitted.
  • Sample Availability: Available from MDPI.

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MDPI and ACS Style

Mojzych, M. Synthesis of 5-(2-aminoethoxy)-3-methyl-1-phenyl-1H-pyrazolo[4,3-E][1,2,4]triazine. Molbank 2005, 2005, M415. https://doi.org/10.3390/M415

AMA Style

Mojzych M. Synthesis of 5-(2-aminoethoxy)-3-methyl-1-phenyl-1H-pyrazolo[4,3-E][1,2,4]triazine. Molbank. 2005; 2005(2):M415. https://doi.org/10.3390/M415

Chicago/Turabian Style

Mojzych, Mariusz. 2005. "Synthesis of 5-(2-aminoethoxy)-3-methyl-1-phenyl-1H-pyrazolo[4,3-E][1,2,4]triazine" Molbank 2005, no. 2: M415. https://doi.org/10.3390/M415

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