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Volumn 43, Issue 45, 2002, Pages 8071-8073

Utility of 4,6-dichloro-2-(methylthio)-5-nitropyrimidine. An efficient solid-phase synthesis of olomoucine

Author keywords

[No Author keywords available]

Indexed keywords

4,6 DICHLORO 2 (METHYLTHIO) 5 NITROPYRIMIDINE; OLOMOUCINE; PHOSPHOTRANSFERASE INHIBITOR; PURINE DERIVATIVE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037020623     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01953-6     Document Type: Article
Times cited : (22)

References (37)
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    • (p) Di Lucrezia, R.; Gilbert, I. H.; Floyd, C. D. J. Comb. Chem. 2000, 2, 249. Solution-phase methodologies have also been reported. For two recent examples, see: (purines from polyhalo purines);
    • (2000) J. Comb. Chem. , vol.2 , pp. 249
    • Di Lucrezia, R.1    Gilbert, I.H.2    Floyd, C.D.3
  • 19
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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.
    • (1990) Aust. J. Chem. , vol.43 , pp. 55
    • Harnden, M.R.1    Hurst, D.T.2
  • 20
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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.
    • (1965) J. Chem. Soc. , pp. 3770
    • Brown, D.J.1    Jacobsen, N.W.2
  • 21
    • 0001052186 scopus 로고
    • For the original report of olomoucine, see: Parker, C. W.; Entsch, B.; Letham, D. S. Phytochemistry 1986, 25, 303. The term olomoucine was coined in 1994 'for convenience', see: Vesely, J. et al. Eur. J. Biochem. 1994, 224, 771.
    • (1986) Phytochemistry , vol.25 , pp. 303
    • Parker, C.W.1    Entsch, B.2    Letham, D.S.3
  • 22
    • 0028093182 scopus 로고
    • For the original report of olomoucine, see: Parker, C. W.; Entsch, B.; Letham, D. S. Phytochemistry 1986, 25, 303. The term olomoucine was coined in 1994 'for convenience', see: Vesely, J. et al. Eur. J. Biochem. 1994, 224, 771.
    • (1994) Eur. J. Biochem. , vol.224 , pp. 771
    • Vesely, J.1
  • 24
    • 0005199658 scopus 로고    scopus 로고
    • The resin used in this work was purchased from Argonaut technologies, see: http://www.argotech.com.
  • 27
    • 0005196030 scopus 로고    scopus 로고
    • In our optimizations of this step, we found reduced temperatures (<50°C) were necessary to avoid displacement of the unactivated thiomethyl moiety.
    • In our optimizations of this step, we found reduced temperatures (<50°C) were necessary to avoid displacement of the unactivated thiomethyl moiety.
  • 34
    • 0033534331 scopus 로고    scopus 로고
    • 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.
    • (1999) Tetrahedron Lett. , vol.40 , pp. 245
    • Hari, A.1    Miller, B.L.2
  • 35
    • 0035943314 scopus 로고    scopus 로고
    • 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.
    • (2001) J. Org. Chem. , vol.66 , pp. 5783
    • Makara, G.M.1    Ewing, W.2    Ma, Y.3    Wintner, E.4
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    • 1H NMR
    • 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.
    • Further work using pyrimidine 1, including applications to library synthesis, has been completed and will be reported in detail shortly.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.