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Syntheses of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine 1: (a) Harnden, M. R.; Hurst, D. T. Aust. J. Chem. 1990, 43, 55; (b) Brown, D. J.; Jacobsen, N. W. J. Chem. Soc. 1965, 3770.
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For recent syntheses, see Refs. 1i and 1n. For bioactivity of olomoucine and related purines, see: Schow, S. R.; Mackman, R. L.; Blum, C. L.; Brooks, E.; Horsma, A. G.; Joly, A.; Kerwar, S. S.; Lee, G.; Shiffman, D.; Nelson, M. G.; Wang, X.; Wick, M. M.; Zhang, X.; Lum, R. T. Bioorg. Med. Chem. Lett. 1997, 7, 2697.
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24
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0005199658
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The resin used in this work was purchased from Argonaut technologies, see: http://www.argotech.com.
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0005196030
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In our optimizations of this step, we found reduced temperatures (<50°C) were necessary to avoid displacement of the unactivated thiomethyl moiety.
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In our optimizations of this step, we found reduced temperatures (<50°C) were necessary to avoid displacement of the unactivated thiomethyl moiety.
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Hari, A.; Miller, B. L. Tetrahedron Lett. 1999, 40, 245. We found it advantageous to add a protic solvent (MeOH) to achieve efficient reduction with our substrate. We also achieved limited success following: Makara, G. M.; Ewing, W.; Ma, Y.; Wintner, E. J. Org. Chem. 2001, 66, 5783. In following the latter work, we found THF/water to be more effective than the reported DCM/water with our substrate.
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0035943314
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Hari, A.; Miller, B. L. Tetrahedron Lett. 1999, 40, 245. We found it advantageous to add a protic solvent (MeOH) to achieve efficient reduction with our substrate. We also achieved limited success following: Makara, G. M.; Ewing, W.; Ma, Y.; Wintner, E. J. Org. Chem. 2001, 66, 5783. In following the latter work, we found THF/water to be more effective than the reported DCM/water with our substrate.
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Makara, G.M.1
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1H NMR
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1H NMR.
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Further work using pyrimidine 1, including applications to library synthesis, has been completed and will be reported in detail shortly.
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Further work using pyrimidine 1, including applications to library synthesis, has been completed and will be reported in detail shortly.
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