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Literature DB >> 12659561

Fluorous synthesis of disubstituted pyrimidines.

Abstract

[reaction: see text] The fluorous synthesis of disubstituted pyrimidines is carried out by attaching 2,4-dichloro-6-methylpyrimidine with 1H,1H,2H,2H-perfluorodecanethiol. The tagged substrate is substituted with 3-(trifluoromethyl)pyrazole followed by thioether oxidation and tag displacement with amines or thiols. The fluorous chain serves as a phase tag for intermediate and product purification over FluoroFlash SPE cartridges.

Entities: Chemical

Mesh：

Substances：
Pyrimidines
Fluorides

Year: 2003 PMID： 12659561 PMCID： PMC1857353 DOI： 10.1021/ol027469e

Source DB: PubMed Journal: Org Lett ISSN： 1523-7052 Impact factor: 6.005

10 in total

1. A concise and traceless linker strategy toward combinatorial libraries of 2,6,9-substituted purines.

Authors: S Ding; N S Gray; Q Ding; P G Schultz
Journal: J Org Chem Date: 2001-11-30 Impact factor: 4.354

2. A combinatorial scaffold approach toward kinase-directed heterocycle libraries.

Authors: Sheng Ding; Nathanael S Gray; Xu Wu; Qiang Ding; Peter G Schultz
Journal: J Am Chem Soc Date: 2002-02-27 Impact factor: 15.419

3. Quasiracemic synthesis: concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine.

Authors: Qisheng Zhang; Alexey Rivkin; Dennis P Curran
Journal: J Am Chem Soc Date: 2002-05-22 Impact factor: 15.419

4. Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis.

Authors: Wei Zhang; Zhiyong Luo; Christine Hiu-Tung Chen; Dennis P Curran
Journal: J Am Chem Soc Date: 2002-09-04 Impact factor: 15.419

5. Solid phase synthesis of purines from pyrimidines.

Authors: R Di Lucrezia; I H Gilbert; C D Floyd
Journal: J Comb Chem Date: 2000 May-Jun

6. Fluorous mixture synthesis: a fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds.

Authors: Z Luo; Q Zhang; Y Oderaotoshi; D P Curran
Journal: Science Date: 2001-03-02 Impact factor: 47.728

6 in total

Fluorous synthesis of disubstituted pyrimidines.

1. A concise and traceless linker strategy toward combinatorial libraries of 2,6,9-substituted purines.

2. A combinatorial scaffold approach toward kinase-directed heterocycle libraries.

3. Quasiracemic synthesis: concepts and implementation with a fluorous tagging strategy to make both enantiomers of pyridovericin and mappicine.

4. Solution-phase preparation of a 560-compound library of individual pure mappicine analogues by fluorous mixture synthesis.

5. Solid phase synthesis of purines from pyrimidines.

6. Fluorous mixture synthesis: a fluorous-tagging strategy for the synthesis and separation of mixtures of organic compounds.

7. Resin-capture and release strategy toward combinatorial libraries of 2,6,9-substituted purines.

8. Fluorous Boc ((F)Boc) carbamates: new amine protecting groups for use in fluorous synthesis.

9. Solid-phase synthesis of 2,4-diaminoquinazoline libraries.

10. Simultaneous preparation of four truncated analogues of discodermolide by fluorous mixture synthesis.

Review 1. Fluorous synthesis of heterocyclic systems.

Review 2. Fluorous tagging strategy for solution-phase synthesis of small molecules, peptides and oligosaccharides.

3. Plate-to-plate fluorous solid-phase extraction for solution-phase parallel synthesis.

4. Fluorous parallel synthesis of a hydantoin/thiohydantoin library.

5. Fluorous synthesis of hydantoins and thiohydantoins.

6. Combination of microwave reactions with fluorous separations in the palladium-catalyzed synthesis of aryl sulfides.