Process for producing 8-fluoropurines

Barrio, Jorge R; Satyamurthy, Nagichettiar; Namavari, Mohammad; Phelps, Michael E

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Title: Process for producing 8-fluoropurines

Abstract

An efficient, regiocontrolled approach to the synthesis of 8-fluoropurines by direct fluorination of purines with dilute elemental fluorine, or acetyl hypofluorite, is provided. In a preferred embodiment, a purine compound is dissolved in a polar solvent and reacted with a dilute mixture of F.sub.2 in He or other inert gas.

Inventors:

Barrio, Jorge R ^[1]; Satyamurthy, Nagichettiar ^[2]; Namavari, Mohammad ^[2]; Phelps, Michael E ^[3]

Agoura Hills, CA
Los Angeles, CA
Encino, CA

Issue Date:: 1999-01-01

Research Org.:: Univ. of California (United States)

OSTI Identifier:: 872106

Patent Number(s):: 5861503

Assignee:: Regents of University of California (Oakland, CA)

Patent Classifications (CPCs):: C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS

Show more

C - CHEMISTRY C07 - ORGANIC CHEMISTRY C07D - HETEROCYCLIC COMPOUNDS
C07D473/00 - Heterocyclic compounds containing purine ring systems

Show less

DOE Contract Number:: FC03-87ER60615

Resource Type:: Patent

Country of Publication:: United States

Language:: English

Subject:: process; producing; 8-fluoropurines; efficient; regiocontrolled; approach; synthesis; direct; fluorination; purines; dilute; elemental; fluorine; acetyl; hypofluorite; provided; preferred; embodiment; purine; compound; dissolved; polar; solvent; reacted; mixture; inert; gas; polar solvent; preferred embodiment; inert gas; acetyl hypofluorite; direct fluorination; regiocontrolled approach; purine compound; dilute mixture; elemental fluorine; dilute elemental; /999/

Citation Formats


                    Barrio, Jorge R, Satyamurthy, Nagichettiar, Namavari, Mohammad, and Phelps, Michael E. Process for producing 8-fluoropurines.  United States: N. p., 1999. 
        Web.

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                    Barrio, Jorge R, Satyamurthy, Nagichettiar, Namavari, Mohammad, & Phelps, Michael E. Process for producing 8-fluoropurines.  United States.

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                    Barrio, Jorge R, Satyamurthy, Nagichettiar, Namavari, Mohammad, and Phelps, Michael E. Fri .  
        "Process for producing 8-fluoropurines".  United States.  https://www.osti.gov/servlets/purl/872106.

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@article{osti_872106,

  title        = {Process for producing 8-fluoropurines},

  author       = {Barrio, Jorge R and Satyamurthy, Nagichettiar and Namavari, Mohammad and Phelps, Michael E},

  abstractNote = {An efficient, regiocontrolled approach to the synthesis of 8-fluoropurines by direct fluorination of purines with dilute elemental fluorine, or acetyl hypofluorite, is provided. In a preferred embodiment, a purine compound is dissolved in a polar solvent and reacted with a dilute mixture of F.sub.2 in He or other inert gas.},

  doi          = {},

  journal      = {},
number       = ,

  volume       = ,

  place        = {United States},

  year         = {1999},

  month        = {1}

}

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Works referenced in this record:

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Synthesis and biochemical properties of 8-amino-6-fluoro-9-.beta.-D-ribofuranosyl-9H-purine
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Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV
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Journal of Medicinal Chemistry, Vol. 33, Issue 3
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Introduction of Fluorine Into the C8 Position of Purine Nucleosides
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Studies of Nucleosides and Nucleotides. XLIX. Synthesis of 8-Fluoroadenosine
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Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine
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Nucleic acid related compounds. III. Facile synthesis of 5-fluorouracil bases and nucleosides by direct fluorination
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Elemental Fluorine to 8-Fluoropurines in One Step
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The Formation of the CF Bond: The Last Twelve Years
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Supplement D2; The Chemistry of Halides, Pseudo‐Halides and Azides
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The Potential Use of Mechanism-Based Enzyme Inactivators in Medicine
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Journal of Enzyme Inhibition, Vol. 2, Issue 2
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2-Fluoroformycin and 2-aminoformycin. Synthesis and biological activity
journal, November 1985

Secrist, John A.; Shortnacy, Anita T.; Montgomery, John A.
Journal of Medicinal Chemistry, Vol. 28, Issue 11
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Comparison of theoretical and experimental approaches to determination of conformation of nucleosides about the glycosidic bond
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Stolarski, Ryszard; Pohorille, Andrzej; Dudycz, Lech
Biochimica et Biophysica Acta (BBA) - Nucleic Acids and Protein Synthesis, Vol. 610, Issue 1
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A direct synthesis of 5-fluorocytosine and its nucleosides using trifluoromethyl hypofluorite
journal, January 1972

Robins, Morris J.; Naik, S. R.
Journal of the Chemical Society, Chemical Communications, Issue 1
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Synthesis of 2′,3′,5′-tris-O-acetyl-8-fluoroadenosine
journal, January 1976

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Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds
journal, October 1983

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Journal of Medicinal Chemistry, Vol. 26, Issue 10
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Regioselective Fluorination of Substituted Guanines with Dilute F ₂ : A Facile Entry to 8-Fluoroguanine Derivatives
journal, January 1996

Barrio, Jorge R.; Namavari, Mohammad; Phelps, Michael E.
The Journal of Organic Chemistry, Vol. 61, Issue 18
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Fluorination of (E)-.beta.-(Fluoromethylene)-m-Tyrosine: Regioselective Synthesis of 4-Fluoro-(E)-.beta.-(Fluoromethylene)-m-Tyrosine
journal, January 1995

Lacan, Goran; Satyamurthy, N.; Barrio, Jorge R.
The Journal of Organic Chemistry, Vol. 60, Issue 1
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Functionalisation including fluorination of caffeine, guanosine tetraacetate, and uridine triacetate using electrochemical oxidation
journal, December 1994

Sono, Masakazu; Toyoda, Naoko; Shizuri, Yoshikazu
Tetrahedron Letters, Vol. 35, Issue 49
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Nucleic acid related compounds. 21. Direct fluorination of uracil and cytosine bases and nucleosides using trifluoromethyl hypofluorite. Mechanism, stereochemistry, and synthetic applications
journal, October 1976

Robins, Morris J.; MacCoss, Malcolm; Naik, S. R.
Journal of the American Chemical Society, Vol. 98, Issue 23
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Regiospecific aromatic fluorodemetallation of group IVb metalloarenes using elemental fluorine or acetyl hypofluorite
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Similar Records

Title: Process for producing 8-fluoropurines

Abstract

Citation Formats

Bimanes. 21. syn-(Methyl fluoro)bimane formation via acetyl hypofluorite journal, October 1985

Novel route to 3(5)-fluoro-1,2,4-triazoles and 8-fluoropurines by displacement of the nitro group journal, December 1973

A direct method for the preparation of 2-hydroxyethoxymethyl derivatives of guanine, adenine, and cytosine journal, May 1980

Nucleic acid related compounds. 34. Non-aqueous diazotization with tert -butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides journal, September 1981

The Direct Conversion of Chloropurines to Fluoropurines 1 journal, September 1963

Studies of nucleosides and nucleotides. journal, February 1974

Methods of Fluorination in Organic Chemistry journal, August 1981

Synthesis and biochemical properties of 8-amino-6-fluoro-9-.beta.-D-ribofuranosyl-9H-purine journal, October 1986

Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV journal, March 1990

A General Approach to Organic Reactivity: The Configuration Mixing Model book, January 1985

Introduction of Fluorine Into the C8 Position of Purine Nucleosides journal, February 1990

Studies of Nucleosides and Nucleotides. XLIX. Synthesis of 8-Fluoroadenosine journal, January 1971

Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine journal, February 1988

Tetrahedron report number 221 journal, January 1987

Nucleic acid related compounds. III. Facile synthesis of 5-fluorouracil bases and nucleosides by direct fluorination journal, October 1971

Elemental Fluorine to 8-Fluoropurines in One Step journal, January 1996

The Formation of the CF Bond: The Last Twelve Years book, September 1995

The Potential Use of Mechanism-Based Enzyme Inactivators in Medicine journal, January 1988

2-Fluoroformycin and 2-aminoformycin. Synthesis and biological activity journal, November 1985

Comparison of theoretical and experimental approaches to determination of conformation of nucleosides about the glycosidic bond journal, November 1980

A direct synthesis of 5-fluorocytosine and its nucleosides using trifluoromethyl hypofluorite journal, January 1972

Synthesis of 2′,3′,5′-tris-O-acetyl-8-fluoroadenosine journal, January 1976

Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds journal, October 1983

Regioselective Fluorination of Substituted Guanines with Dilute F 2 : A Facile Entry to 8-Fluoroguanine Derivatives journal, January 1996

Fluorination of (E)-.beta.-(Fluoromethylene)-m-Tyrosine: Regioselective Synthesis of 4-Fluoro-(E)-.beta.-(Fluoromethylene)-m-Tyrosine journal, January 1995

Functionalisation including fluorination of caffeine, guanosine tetraacetate, and uridine triacetate using electrochemical oxidation journal, December 1994

Nucleic acid related compounds. 21. Direct fluorination of uracil and cytosine bases and nucleosides using trifluoromethyl hypofluorite. Mechanism, stereochemistry, and synthetic applications journal, October 1976

Regiospecific aromatic fluorodemetallation of group IVb metalloarenes using elemental fluorine or acetyl hypofluorite journal, June 1987

Substitutions and Additions in the Heterocyclic Rings of Nucleic Acid Bases and their Derivatives book, January 1972

Fluorinated Substrate Analogs: Routes of Metabolism and Selective Toxicity book, January 1983

Electrophilic and nucleophilic approaches to the synthesis of 3-fluorodiazepam journal, June 1987

Functionalization Including Fluorination of Nitrogen-Containing Compounds Using Electrochemical Oxidation. journal, January 1996

Remote and selective electrophilic fluorinations at the carbon-hydrogen single bond journal, October 1980

Bimanes. 21. syn-(Methyl fluoro)bimane formation via acetyl hypofluorite
journal, October 1985

Novel route to 3(5)-fluoro-1,2,4-triazoles and 8-fluoropurines by displacement of the nitro group
journal, December 1973

A direct method for the preparation of 2-hydroxyethoxymethyl derivatives of guanine, adenine, and cytosine
journal, May 1980

Nucleic acid related compounds. 34. Non-aqueous diazotization with tert -butyl nitrite. Introduction of fluorine, chlorine, and bromine at C-2 of purine nucleosides
journal, September 1981

The Direct Conversion of Chloropurines to Fluoropurines ¹
journal, September 1963

Studies of nucleosides and nucleotides.
journal, February 1974

Methods of Fluorination in Organic Chemistry
journal, August 1981

Synthesis and biochemical properties of 8-amino-6-fluoro-9-.beta.-D-ribofuranosyl-9H-purine
journal, October 1986

Acid-stable 2'-fluoro purine dideoxynucleosides as active agents against HIV
journal, March 1990

A General Approach to Organic Reactivity: The Configuration Mixing Model
book, January 1985

Introduction of Fluorine Into the C8 Position of Purine Nucleosides
journal, February 1990

Studies of Nucleosides and Nucleotides. XLIX. Synthesis of 8-Fluoroadenosine
journal, January 1971

Synthesis and biological evaluations of certain 2-halo-2'-substituted derivatives of 9-.beta.-D-arabinofuranosyladenine
journal, February 1988

Tetrahedron report number 221
journal, January 1987

Nucleic acid related compounds. III. Facile synthesis of 5-fluorouracil bases and nucleosides by direct fluorination
journal, October 1971

Elemental Fluorine to 8-Fluoropurines in One Step
journal, January 1996

The Formation of the CF Bond: The Last Twelve Years
book, September 1995

The Potential Use of Mechanism-Based Enzyme Inactivators in Medicine
journal, January 1988

2-Fluoroformycin and 2-aminoformycin. Synthesis and biological activity
journal, November 1985

Comparison of theoretical and experimental approaches to determination of conformation of nucleosides about the glycosidic bond
journal, November 1980

A direct synthesis of 5-fluorocytosine and its nucleosides using trifluoromethyl hypofluorite
journal, January 1972

Synthesis of 2′,3′,5′-tris-O-acetyl-8-fluoroadenosine
journal, January 1976

Synthesis and biological evaluation of 2-fluoro-8-azaadenosine and related compounds
journal, October 1983

Regioselective Fluorination of Substituted Guanines with Dilute F ₂ : A Facile Entry to 8-Fluoroguanine Derivatives
journal, January 1996

Fluorination of (E)-.beta.-(Fluoromethylene)-m-Tyrosine: Regioselective Synthesis of 4-Fluoro-(E)-.beta.-(Fluoromethylene)-m-Tyrosine
journal, January 1995

Functionalisation including fluorination of caffeine, guanosine tetraacetate, and uridine triacetate using electrochemical oxidation
journal, December 1994

Nucleic acid related compounds. 21. Direct fluorination of uracil and cytosine bases and nucleosides using trifluoromethyl hypofluorite. Mechanism, stereochemistry, and synthetic applications
journal, October 1976

Regiospecific aromatic fluorodemetallation of group IVb metalloarenes using elemental fluorine or acetyl hypofluorite
journal, June 1987

Substitutions and Additions in the Heterocyclic Rings of Nucleic Acid Bases and their Derivatives
book, January 1972

Fluorinated Substrate Analogs: Routes of Metabolism and Selective Toxicity
book, January 1983

Electrophilic and nucleophilic approaches to the synthesis of 3-fluorodiazepam
journal, June 1987

Functionalization Including Fluorination of Nitrogen-Containing Compounds Using Electrochemical Oxidation.
journal, January 1996

Remote and selective electrophilic fluorinations at the carbon-hydrogen single bond
journal, October 1980