Document Detail

Nucleic acid related compounds. 118. Nonaqueous diazotization of aminopurine derivatives. Convenient access to 6-halo- and 2,6-dihalopurine nucleosides and 2'-deoxynucleosides with acyl or silyl halides.
MedLine Citation:
PMID:  12530909     Owner:  NLM     Status:  MEDLINE    
Treatment of 9-(2,3,5-tri-O-acetyl-beta-d-ribofuranosyl)-2-amino-6-chloropurine (1) with TMS-Cl and benzyltriethylammonium nitrite (BTEA-NO2) in dichloromethane gave the crystalline 2,6-dichloropurine nucleoside 2, and acetyl chloride/BTEA-NO2 was equally effective ( approximately 85%, without chromatography). TMS-Br/tert-butyl nitrite/dibromomethane gave crystalline 2-bromo-6-chloro analogue 3 (85%). (Chloro or bromo)-dediazoniation of 3',5'-di-O-acetyl-2'-deoxyadenosine (4) gave the 6-[chloro (5, 63%) or bromo (6, 80%)]purine deoxynucleosides, and 2',3',5'-tri-O-acetyladenosine (8) was converted into the 6-chloropurine nucleoside 9 (71%).
Paula Francom; Morris J Robins
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Publication Detail:
Type:  Journal Article; Research Support, Non-U.S. Gov't    
Journal Detail:
Title:  The Journal of organic chemistry     Volume:  68     ISSN:  0022-3263     ISO Abbreviation:  J. Org. Chem.     Publication Date:  2003 Jan 
Date Detail:
Created Date:  2003-01-17     Completed Date:  2003-07-07     Revised Date:  2006-11-15    
Medline Journal Info:
Nlm Unique ID:  2985193R     Medline TA:  J Org Chem     Country:  United States    
Other Details:
Languages:  eng     Pagination:  666-9     Citation Subset:  IM    
Department of Chemistry and Biochemistry, Brigham Young University, Provo, Utah 84602-5700, USA.
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MeSH Terms
Chromatography, Thin Layer
Indicators and Reagents
Magnetic Resonance Spectroscopy
Molecular Structure
Nucleic Acids / chemistry*
Purine Nucleosides / analysis,  chemical synthesis*,  chemistry*
Reg. No./Substance:
0/9-(2,3,5-tri-O-acetylribofuranosyl)-2-amino-6-chloropurine; 0/Indicators and Reagents; 0/Nucleic Acids; 0/Purine Nucleosides

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