Ag-Assisted Fluorination of Unprotected 4,6-Disubstituted 2-Aminopyrimidines with Selectfluor

Chenxi Wang; Juewang Cai; Min Zhang; Xiaoming Zhao

doi:10.1021/acs.joc.6b02624

Ag-Assisted Fluorination of Unprotected 4,6-Disubstituted 2-Aminopyrimidines with Selectfluor

Chenxi Wang
, Juewang Cai
, Min Zhang
, Xiaoming Zhao^*

^*Corresponding author for this work

Tongji University

Research output: Contribution to journal › Article › peer-review

28 Scopus citations

Abstract

A direct fluorination of 4,6-disubstituted 2-aminopyrimidines with Selectfluor in the presence of Ag(I) is presented, affording the corresponding 4,6-disubstituted 5-fluoro-2-aminopyrimidines with acceptable to high yield. Ag(I) is crucial for this chemoselective fluorination process. The transformation of 4,6-diphenyl 5-fluoro-2-aminopyrimidine into N-(5-fluoro-4,6-diphenylpyrimidin-2-yl)-4-methylbenzenesulfonamide is discussed, and the reaction mechanism is investigated, as well.

Original language	English
Pages (from-to)	1260-1265
Number of pages	6
Journal	Journal of Organic Chemistry
Volume	82
Issue number	2
DOIs	https://doi.org/10.1021/acs.joc.6b02624
State	Published - 20 Jan 2017
Externally published	Yes

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title = "Ag-Assisted Fluorination of Unprotected 4,6-Disubstituted 2-Aminopyrimidines with Selectfluor",

abstract = "A direct fluorination of 4,6-disubstituted 2-aminopyrimidines with Selectfluor in the presence of Ag(I) is presented, affording the corresponding 4,6-disubstituted 5-fluoro-2-aminopyrimidines with acceptable to high yield. Ag(I) is crucial for this chemoselective fluorination process. The transformation of 4,6-diphenyl 5-fluoro-2-aminopyrimidine into N-(5-fluoro-4,6-diphenylpyrimidin-2-yl)-4-methylbenzenesulfonamide is discussed, and the reaction mechanism is investigated, as well.",

author = "Chenxi Wang and Juewang Cai and Min Zhang and Xiaoming Zhao",

note = "Publisher Copyright: {\textcopyright} 2016 American Chemical Society.",

year = "2017",

month = jan,

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doi = "10.1021/acs.joc.6b02624",

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T1 - Ag-Assisted Fluorination of Unprotected 4,6-Disubstituted 2-Aminopyrimidines with Selectfluor

AU - Wang, Chenxi

AU - Cai, Juewang

AU - Zhang, Min

AU - Zhao, Xiaoming

PY - 2017/1/20

Y1 - 2017/1/20

N2 - A direct fluorination of 4,6-disubstituted 2-aminopyrimidines with Selectfluor in the presence of Ag(I) is presented, affording the corresponding 4,6-disubstituted 5-fluoro-2-aminopyrimidines with acceptable to high yield. Ag(I) is crucial for this chemoselective fluorination process. The transformation of 4,6-diphenyl 5-fluoro-2-aminopyrimidine into N-(5-fluoro-4,6-diphenylpyrimidin-2-yl)-4-methylbenzenesulfonamide is discussed, and the reaction mechanism is investigated, as well.

AB - A direct fluorination of 4,6-disubstituted 2-aminopyrimidines with Selectfluor in the presence of Ag(I) is presented, affording the corresponding 4,6-disubstituted 5-fluoro-2-aminopyrimidines with acceptable to high yield. Ag(I) is crucial for this chemoselective fluorination process. The transformation of 4,6-diphenyl 5-fluoro-2-aminopyrimidine into N-(5-fluoro-4,6-diphenylpyrimidin-2-yl)-4-methylbenzenesulfonamide is discussed, and the reaction mechanism is investigated, as well.

UR - https://www.scopus.com/pages/publications/85018668759

U2 - 10.1021/acs.joc.6b02624

DO - 10.1021/acs.joc.6b02624

M3 - 文章

C2 - 28002944

AN - SCOPUS:85018668759

SN - 0022-3263

VL - 82

SP - 1260

EP - 1265

JO - Journal of Organic Chemistry

JF - Journal of Organic Chemistry

IS - 2

ER -

Ag-Assisted Fluorination of Unprotected 4,6-Disubstituted 2-Aminopyrimidines with Selectfluor

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