Elemental fluorine to 8-fluoropurines in one step

Journal Article · Tue Oct 29 23:00:00 EST 1996 · Journal of the American Chemical Society

DOI:https://doi.org/10.1021/ja961456c· OSTI ID:420727

Barrio, J R; Namavari, M; Phelps, M E; Satyamurthy, N ^[1]

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1. Univ. of California, Los Angeles, CA (United States)

An efficient regiocontrolled approach to the synthesis of 8-fluoropurines by direct fluorination of purines with dilute elemental fluorine is described. The one-step procedure produced regiospecific substitution of the C(8)-hydrogen of purine derivatives in isolated yields close to 30% with protected purines in CHCl{sub 3}. Fluorination yields with unprotected purines in EtOH were reduced to less than 10%. The electrophilic fluorination procedure has a broad scope of applicability and permits a ready and easy access to 8-fluoropurine derivatives, for the first time, for evaluation of their biochemical and pharmacological properties. 42 refs., 2 tabs.

• DOE Contract Number: FC03-87ER60615
• OSTI ID: 420727
• Journal Information: Journal of the American Chemical Society, Journal Name: Journal of the American Chemical Society Journal Issue: 43 Vol. 118; ISSN JACSAT; ISSN 0002-7863
• Country of Publication: United States
• Language: English

Related Subjects

36 MATERIALS SCIENCE
40 CHEMISTRY
55 BIOLOGY AND MEDICINE
BASIC STUDIES
BIOCHEMISTRY
FLUORINATION
FLUORINE 19
HYDROGEN 1
NUCLEAR MAGNETIC RESONANCE
NUMERICAL DATA
PHARMACOLOGY
PURINES
SYNTHESIS