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For other methods to potentially access 2-amino-4-heteroarylpyrimidines, see: Collis, A. J.; Foster, M. L.; Halley, F.; Maslen, C.; McLay, I. M.; Page, K. M.; Redford, E. J.; Souness, J. E.; Wilsher, N. E. Bioorg. Med. Chem. Lett. 2001, 11, 693.
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Manley, P. J.; Balitza, A. E.; Bilodeau, M. T.; Coll, K. E.; Hartman, G. E.; McFall, R. C.; Rickert, K. W.; Rodman, L. D.; Thomas, K. A. Bioorg. Med. Chem. Lett. 2003, 13, 1673.
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Clark, M. P.; Laughlin, S. K.; Laufersweiler, M. J.; Bookland, R. G.; Brugel, T. A.; Golebiowski, A.; Sabat, M. P.; Townes, J. A.; VanRens, J. C.; Djung, J. F.; Natchus, M. G.; De, B.; Hsieh, L. C.; Xu, S. C.; Walter, R. L.; Mekel, M. J.; Heitmeyer, S. A.; Brown, K. K.; Juergens, K.; Taiwo, Y. O.; Janusz, M. J. J. Med. Chem. 2004, 47, 2724.
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84986532359
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Strekowski, L.; Harden, D. B.; Grubb, W. B., III; Patterson, S. E.; Czarny, A.; Mokrosz, M. J.; Cegla, M. T.; Wydra, R. L. J. Heterocycl. Chem. 1990, 27, 1393.
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13
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25444523433
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note
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A SciFinder search of the generic 2-amino acid-4-cyclic-pyrimidine scaffold identified a total of only 18 patents and 2 publications. In ref 2, Clark et al., one of the 30 compounds exemplified was a 2-Phe-OMe-4-cyclic- pyrimidine.
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14
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25444462967
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note
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Resynthesis of 8a and 8c with the enantiomerically pure amino acids and subsequent purification via preparatory HPLC revealed a minimal degree of epimerization. The desired products 8a and 8c were isolated in 93% and 76% respective chiral purity.
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15
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0029918554
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Barn, D.R.1
Morphy, J.R.2
Rees, D.C.3
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