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Short Note

Synthesis of 6-Chloro-N,N,N',N'-tetrakis-pyridin-2-ylmethyl-[1,3,5]triazine-2,4-diamine

Institute of Organic Chemistry, University of Regensburg, D-93040 Regensburg, Germany
*
Author to whom correspondence should be addressed.
Molbank 2007, 2007(4), M556; https://doi.org/10.3390/M556
Submission received: 2 August 2007 / Accepted: 6 September 2007 / Published: 7 September 2007
Transition metal complexes of pyridine-containing ligands are widely used in catalysis [1], supramolecular self-assembly [2], and anion recognition [3]. Binuclear Zn2+-2,2’-dipicolylamine (dpa) complexes are particular useful for the binding of phosphorylated peptides in aqueous solution under physiological pH with high affinity and selectivity [4,5,6,7,8,9]. Similar ligands based on 2,2’-bipyridylamine (bpa) and 2,4,6-tris-chloro-triazine, have been used to form coordination networks with copper(II) ions. In these compounds the bpa moiety is attached directly to the hetero-aromatic core. Combination of 2,4,6-tris-chloro-triazine with dpa moieties leads to a new hybrid compound B, which should be used in phosphate binding studies. We describe the versatile short synthesis of the dpa compound B starting from 2,4,6-tris-chloro-triazine A.
Molbank 2007 m556 i001
2,4,6-Tris-chloro-triazine (A, 3 g, 16.3 mmol) was dissolved in 120 mL of acetone and di-(pyridylmethyl) amine (dpa; 6.49 g, 32.6 mmol) and K2CO3 (9 g, 65.2 mmol) were added subsequently. The reaction mixture was refluxed for 24 h and the insoluble parts were filtered off. The mixed was poured onto crushed ice and stirred for 15 min at room temp., water was added and the mixture stirred for an additional 15 min. The product was obtained by filtration as a pale yellow solid (2.9 g, 35%).
Melting point: > 200°C
1H-NMR (300 MHz, CDCl3): δ = 4.82 (s, 4 H, CH2), 5.03 (s, 4 H, CH2), 6.90 (d, 3J = 8.0 Hz, 2 H), 7.04 (t, 3J = 5.8 Hz, 2 H), 7.16 (t, 3J = 5.6 Hz, 2 H), 7.31 (d, 3J = 8.0 Hz, 2 H), 7.38 (t, 3J = 7.7 Hz, 2 H), 7.64 (t, 3J = 7.7 Hz, 2 H), 8.41 (d, 3J = 4.1 Hz, 2 H), 8.51 (d, 3J = 4.9, 2 H). 13C-NMR (75 MHz, CDCl3): δ = 51.9 (-, 2 C), 52.1 (-, 2 C), 121.3-122.5 (+, 8 C), 136.7 (+, 2 C), 136. 7 (+, 2 C), 149.2 (+, 2 C), 149.3 (+, 2 C), 157.2 (Cquat, 2 C), 157.2 (Cquat, 2 C), 165.7 (Cquat, 2 C), 169.9 (Cquat, 1 C).
ES-MS (DCM/MeOH + 10 mmol/l NH4Ac): m/z (%) = 510.3 (100) [MH+].
Elemental analysis: Calc. C 63.59, H 4.74, N 24.72 found C 63.27, H 4.72, N 24.58; IR (KBr) n (cm-1) = 2927 (w), 2529 (w), 1707 (s), 1571 (s), 1491 (m), 1433 (w), 1410 (w), 1354 (w), 1319 (w), 1237 (w), 1169 (w), 1084 (w), 1048 (w), 972 (w), 947 (w), 889 (w), 863 (w), 804 (w), 756 (m), 683 (w), 617 (w), 554 (w), 458 (w).

Conclusion

A new dpa compound B was prepared in a one step synthesis. The compound can be prepared from commercially available compounds and is accessible by a simple reaction. Surprisingly, in first attempts this compound did not form spontaneously complexes with Zn2+ salts at conditions described for other dpa ligands [4,5,6,7,8,9].

Supplementary materials

Supplementary File 1Supplementary File 2Supplementary File 3

References

  1. Gil-Molto, J.; Karlstroem, S.; Najera, C. Tetrahedron 2005, 61(51), 12168–12176.
  2. Demeshko, S.; Leibeling, G.; Dechert, S.; Meyer, F. Dalton Trans. 2004, (21), 3782–7.
  3. Kruppa, M.; Koenig, B. Chem. Rev. 2006, 106(9), 3520–60. [PubMed]
  4. Jiang, H.; O'Neil E, J.; Divittorio, K. M.; Smith, B. D. Org. Lett. 2005, 7(14), 3013–6. [PubMed]
  5. Ojida, A.; Inoue, M. A.; Mito-Oka, Y.; Hamachi, I. J. Am. Chem. Soc. 2003, 125(34), 10184–5. [CrossRef] [PubMed]
  6. Ojida, A.; Mito-Oka, Y.; Inoue, M. A.; Hamachi, I. J. Am. Chem. Soc. 2002, 124(22), 6256–8. [CrossRef]
  7. Ojida, A.; Miyahara, Y.; Kohira, T.; Hamachi, I. Biopolymers 2004, 76(2), 177–184. [PubMed]
  8. Ojida, A.; Park, S.-k.; Mito-oka, Y.; Hamachi, I. Tetrahedron Lett. 2002, 43(35), 6193–9195.
  9. Yamaguchi, S.; Yoshimura, I.; Kohira, T.; Tamaru, S.; Hamachi, I. J. Am. Chem. Soc. 2005, 127(33), 11835–41. [CrossRef] [PubMed]
Figure 1. 1H-NMR spectrum of compound B
Figure 1. 1H-NMR spectrum of compound B
Molbank 2007 m556 g001
Figure 2. X-ray structure of B. Suitable crystals were obtained by recrystallization from DCM/MeOH 5:1.
Figure 2. X-ray structure of B. Suitable crystals were obtained by recrystallization from DCM/MeOH 5:1.
Molbank 2007 m556 g002

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MDPI and ACS Style

Vomasta, D.; Zabel, M.; König, B. Synthesis of 6-Chloro-N,N,N',N'-tetrakis-pyridin-2-ylmethyl-[1,3,5]triazine-2,4-diamine. Molbank 2007, 2007, M556. https://doi.org/10.3390/M556

AMA Style

Vomasta D, Zabel M, König B. Synthesis of 6-Chloro-N,N,N',N'-tetrakis-pyridin-2-ylmethyl-[1,3,5]triazine-2,4-diamine. Molbank. 2007; 2007(4):M556. https://doi.org/10.3390/M556

Chicago/Turabian Style

Vomasta, Daniel, Manfred Zabel, and Burkhard König. 2007. "Synthesis of 6-Chloro-N,N,N',N'-tetrakis-pyridin-2-ylmethyl-[1,3,5]triazine-2,4-diamine" Molbank 2007, no. 4: M556. https://doi.org/10.3390/M556

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