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Synthesis of novel 4-(2-amino-5-thiazolyl)-pyrimidine-2-amines as potential protein kinase inhibitors

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Abstract

A short and efficient sequence for the synthesis of a series of 4-(2-amino-5-thiazolyl)-pyrimidine-2-amines was developed. 1-Phenyl-2-(6-pyrimidinyl)-ethanones, obtained via Weinreb’s methodology, were used in a Hantzsch thiazole cyclization reaction, followed by introduction of the aniline moieties via nucleophilic substitution.

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References

  1. Zimmermann J (1995) PCT Int Appl WO 9509853 CAN 123:55914

  2. Zimmermann J (1993) Eur Pat Appl EP 564409 CAN 120:107056

  3. Buchdunger E, Zimmermann J, Mett H, Meyer T, Muller M, Druker BJ, Lydon NB (1996) Cancer Res 56:100

    CAS  Google Scholar 

  4. Druker BJ, Tamura S, Buchdunger E, Ohno S, Segal GM, Fanning S, Zimmermann J, Lydon NB (1996) Nat Med 2:561

    Article  CAS  Google Scholar 

  5. Furet P, Zimmermann J, Capraro HG, Meyer T, Imbach P (2000) J Comput Aided Mol Des 14:403

    Article  CAS  Google Scholar 

  6. Eberle M, Stierli D, Pillonel C, Ziegler H (2001) PCT Int Appl WO 2001093682 CAN 136:33324

    Google Scholar 

  7. Pillonel C (2005) Pest Manag Sci 61:1069

    Article  CAS  Google Scholar 

  8. Stanetty P, Röhrling J, Schnürch M, Mihovilovic MD (2006) Tetrahedron 62:2380

    Article  CAS  Google Scholar 

  9. Stanetty P, Hattinger G, Schnürch M, Mihovilovic MD (2005) J Org Chem 70:5215

    Article  CAS  Google Scholar 

  10. Hattinger G, Stanetty P, Eberle M (Syngenta Participations A.-G., Switz.) (2002) Br UK Pat Appl GB 2369359 CAN 137:216957

  11. Mueller U, Eberle M, Pillonel C, Lutz W, Stanetty P (2003) PCT Int Appl WO 2003029249A1 CAN 138:304297

  12. Rupert KC, Henry JR, Dodd JH, Wadsworth SA, Cavender DE, Olini GC, Fahmy B, Siekierka JJ (2003) Bioorg Med Chem Lett 13:347

    Article  CAS  Google Scholar 

  13. Dodd JH, Henry JR, Rupert KC (2001) PCT Int Appl WO 2001034605 CAN 134:366888

  14. Almansa Rosales C, Virgili Bernado M (2004) PCT Int Appl WO 2004076450 CAN 141:260745

  15. Nahm S, Weinreb SM (1981) Tetrahedron Lett 39:3815

    Article  Google Scholar 

  16. Li X, Hewgley JB, Mulrooney CA, Yang J, Kozlowski MC (2003) J Org Chem 68:5500

    Article  CAS  Google Scholar 

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Acknowledgments

We thank Syngenta Crop Protection, Basel, for generous financial support.

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Correspondence to Peter Stanetty.

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Sušnik, M.P., Schnürch, M., Mihovilovic, M.D. et al. Synthesis of novel 4-(2-amino-5-thiazolyl)-pyrimidine-2-amines as potential protein kinase inhibitors. Monatsh Chem 140, 423–430 (2009). https://doi.org/10.1007/s00706-008-0047-9

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  • DOI: https://doi.org/10.1007/s00706-008-0047-9

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