Convenient synthesis of 2,9-disubstituted guanines mediated by solid- supported reagents

Tetrahedron Letters

Volumn 41, Issue 19, 2000, Pages 3573-3576

  McComas, Warren ^a   Chen, Li ^a   Kim, Kyungjin ^a  

^a HOFFMANN LA ROCHE INC   (United States)

Author keywords

Combinatorial chemistry; Purines; Supported reagents

Indexed keywords

ACICLOVIR; ANTIVIRUS AGENT; BUCICLOVIR; GANCICLOVIR; GUANINE DERIVATIVE; PURINE DERIVATIVE; REAGENT;

ANTIVIRAL ACTIVITY; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; ISOMERISM; LIQUID CHROMATOGRAPHY; MASS SPECTROMETRY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 0034612060     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00466-4     Document Type: Article

References (19)

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10. 6-Benzyl-2-aminopurine 4 was prepared in large scale from commercially available 2-amino-6-chloropurine according to the precedent: Chae, M. Y.; McDougall, M. G.; Dolan, M. E.; Swenn, K.; Pegg, A. E.; Moschel, R. C. J. Med. Chem. 1994, 37, 342-347.
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13. 1H NMR signal, which for the N7 isomer appears slightly downfield from that of the N9 isomer: Raju, N.; Robins, R. K.; Vaghefi, M. M. J. Chem. Soc., Chem. Commun. 1989, 1769-1770 and references cited therein.
14. The purity of the N7 isomer determined by LC/MS (ELSD) varied between 60 and 96% depending on the alkylating reagents. Due to space limitations, more details will be provided in a full account of this work.
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17. 2O containing 0.02% TFA and monitored at 215 nm using a UV detector and by a SEDEX 55 evaporative light scattering detector (ELSD). Purity scores reported herein are based on ELSD.
18. ™.
19. 13C NMR, and mass spectrometry (FAB).