Preparation of 4,6-disubstituted 5-pyrimidinesulfonamides

Wayne M. Best; Marie Anne M. Fam; Martin J. Gregory; Bruno Kasum; Philip L. Keep; Sam Lazzaro; Nicole Osner; Natasha Stewart; San H. Thang; Keith G. Watson

Preparation of 4,6-disubstituted 5-pyrimidinesulfonamides

Wayne M. Best, Marie Anne M. Fam, Martin J. Gregory, Bruno Kasum, Philip L. Keep, Sam Lazzaro, Nicole Osner, Natasha Stewart, San H. Thang, Keith G. Watson

School of Chemistry

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

2 Citations (Scopus)

Abstract

The first general synthesis of 4,6-disubstituted 5-pyrimidinesulfonamides is described. Treatment of 4,6-dichloro-5-benzylthiopyrimidine (3) with ethoxide or trifluoroethoxide, oxidation of the benzylthio group to a sulfonyl chloride and reaction with ammonia gave 4,6-dialkoxy-5-pyrimidinesulfonamides 5a,b. Stepwise displacement of the trifluoroethoxy groups in 5a gave a variety of symmetrical and non-symmetrical 4,6-disubstituted 5-pyrimidinesulfonamides 5b-h.

Original language	English
Pages (from-to)	36-38
Number of pages	3
Journal	Synthesis
Issue number	1
Publication status	Published - 1 Jan 1998

Keywords

Nucleophilic
Pyrimidine
Substitution
Sulfonamides
Trifluoroethoxy

Cite this

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title = "Preparation of 4,6-disubstituted 5-pyrimidinesulfonamides",

abstract = "The first general synthesis of 4,6-disubstituted 5-pyrimidinesulfonamides is described. Treatment of 4,6-dichloro-5-benzylthiopyrimidine (3) with ethoxide or trifluoroethoxide, oxidation of the benzylthio group to a sulfonyl chloride and reaction with ammonia gave 4,6-dialkoxy-5-pyrimidinesulfonamides 5a,b. Stepwise displacement of the trifluoroethoxy groups in 5a gave a variety of symmetrical and non-symmetrical 4,6-disubstituted 5-pyrimidinesulfonamides 5b-h.",

keywords = "Nucleophilic, Pyrimidine, Substitution, Sulfonamides, Trifluoroethoxy",

author = "Best, \{Wayne M.\} and Fam, \{Marie Anne M.\} and Gregory, \{Martin J.\} and Bruno Kasum and Keep, \{Philip L.\} and Sam Lazzaro and Nicole Osner and Natasha Stewart and Thang, \{San H.\} and Watson, \{Keith G.\}",

year = "1998",

month = jan,

day = "1",

language = "English",

pages = "36--38",

journal = "Synthesis",

issn = "0039-7881",

publisher = "Georg Thieme",

number = "1",

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TY - JOUR

T1 - Preparation of 4,6-disubstituted 5-pyrimidinesulfonamides

AU - Best, Wayne M.

AU - Fam, Marie Anne M.

AU - Gregory, Martin J.

AU - Kasum, Bruno

AU - Keep, Philip L.

AU - Lazzaro, Sam

AU - Osner, Nicole

AU - Stewart, Natasha

AU - Thang, San H.

AU - Watson, Keith G.

PY - 1998/1/1

Y1 - 1998/1/1

N2 - The first general synthesis of 4,6-disubstituted 5-pyrimidinesulfonamides is described. Treatment of 4,6-dichloro-5-benzylthiopyrimidine (3) with ethoxide or trifluoroethoxide, oxidation of the benzylthio group to a sulfonyl chloride and reaction with ammonia gave 4,6-dialkoxy-5-pyrimidinesulfonamides 5a,b. Stepwise displacement of the trifluoroethoxy groups in 5a gave a variety of symmetrical and non-symmetrical 4,6-disubstituted 5-pyrimidinesulfonamides 5b-h.

AB - The first general synthesis of 4,6-disubstituted 5-pyrimidinesulfonamides is described. Treatment of 4,6-dichloro-5-benzylthiopyrimidine (3) with ethoxide or trifluoroethoxide, oxidation of the benzylthio group to a sulfonyl chloride and reaction with ammonia gave 4,6-dialkoxy-5-pyrimidinesulfonamides 5a,b. Stepwise displacement of the trifluoroethoxy groups in 5a gave a variety of symmetrical and non-symmetrical 4,6-disubstituted 5-pyrimidinesulfonamides 5b-h.

KW - Nucleophilic

KW - Pyrimidine

KW - Substitution

KW - Sulfonamides

KW - Trifluoroethoxy

UR - https://www.scopus.com/pages/publications/0031984176

M3 - Article

AN - SCOPUS:0031984176

SN - 0039-7881

SP - 36

EP - 38

JO - Synthesis

JF - Synthesis

IS - 1

ER -

Preparation of 4,6-disubstituted 5-pyrimidinesulfonamides

Abstract

Keywords

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