Fluorous Synthesis of Disubstituted Pyrimidines

Overview

Journal Org Lett

Publisher American Chemical Society

Specialties Biochemistry
Chemistry

Date 2003 Mar 28

PMID 12659561

Citations 10

Authors

Wei Zhang

Affiliations

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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.

Citing Articles

One-Pot Synthesis of 1-Aryl-3-trifluoromethylpyrazoles Using Nitrile Imines and Mercaptoacetaldehyde As a Surrogate of Acetylene.

Swiatek K, Utecht-Jarzynska G, Palusiak M, Ma J, Jasinski M Org Lett. 2023; 25(24):4462-4467.

PMID: 37309990 PMC: 10294255. DOI: 10.1021/acs.orglett.3c01437.

Synthetic applications of fluorous solid-phase extraction (F-SPE).

Zhang W, Curran D Tetrahedron. 2008; 62(51):11837-11865.

PMID: 18509513 PMC: 2396515. DOI: 10.1016/j.tet.2006.08.051.

Fluorous synthesis of sclerotigenin-type benzodiazepine-quinazolinones.

Zhang W, Williams J, Lu Y, Nagashima T, Chu Q Tetrahedron Lett. 2007; 48(4):563-565.

PMID: 17479166 PMC: 1865100. DOI: 10.1016/j.tetlet.2006.11.127.

Automation of fluorous solid-phase extraction for parallel synthesis.

Zhang W, Lu Y J Comb Chem. 2006; 8(6):890-6.

PMID: 17096578 PMC: 1934609. DOI: 10.1021/cc0601130.

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

Zhang W, Lu Y, Nagashima T J Comb Chem. 2005; 7(6):893-7.

PMID: 16283798 PMC: 1857349. DOI: 10.1021/cc050061z.

References

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