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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Zimmermann J (1995) PCT Int Appl WO 9509853 CAN 123:55914
Zimmermann J (1993) Eur Pat Appl EP 564409 CAN 120:107056
Buchdunger E, Zimmermann J, Mett H, Meyer T, Muller M, Druker BJ, Lydon NB (1996) Cancer Res 56:100
Druker BJ, Tamura S, Buchdunger E, Ohno S, Segal GM, Fanning S, Zimmermann J, Lydon NB (1996) Nat Med 2:561
Furet P, Zimmermann J, Capraro HG, Meyer T, Imbach P (2000) J Comput Aided Mol Des 14:403
Eberle M, Stierli D, Pillonel C, Ziegler H (2001) PCT Int Appl WO 2001093682 CAN 136:33324
Pillonel C (2005) Pest Manag Sci 61:1069
Stanetty P, Röhrling J, Schnürch M, Mihovilovic MD (2006) Tetrahedron 62:2380
Stanetty P, Hattinger G, Schnürch M, Mihovilovic MD (2005) J Org Chem 70:5215
Hattinger G, Stanetty P, Eberle M (Syngenta Participations A.-G., Switz.) (2002) Br UK Pat Appl GB 2369359 CAN 137:216957
Mueller U, Eberle M, Pillonel C, Lutz W, Stanetty P (2003) PCT Int Appl WO 2003029249A1 CAN 138:304297
Rupert KC, Henry JR, Dodd JH, Wadsworth SA, Cavender DE, Olini GC, Fahmy B, Siekierka JJ (2003) Bioorg Med Chem Lett 13:347
Dodd JH, Henry JR, Rupert KC (2001) PCT Int Appl WO 2001034605 CAN 134:366888
Almansa Rosales C, Virgili Bernado M (2004) PCT Int Appl WO 2004076450 CAN 141:260745
Nahm S, Weinreb SM (1981) Tetrahedron Lett 39:3815
Li X, Hewgley JB, Mulrooney CA, Yang J, Kozlowski MC (2003) J Org Chem 68:5500
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We thank Syngenta Crop Protection, Basel, for generous financial support.
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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