4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via 
Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines

Viktoras Masevicius; Grazina Petraityte; Sigitas Tumkevicius

doi:10.1055/s-0031-1290524

Synthesis, Inhaltsverzeichnis

Synthesis 2012; 44(9): 1329-1338
DOI: 10.1055/s-0031-1290524

paper

4-Amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via Mitsunobu Reaction of 4-Amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-Mesyl- and N-Nosylarylamines

Viktoras Masevicius

Vilnius University, Department of Organic Chemistry, Vilnius 03225, Lithuania, Fax: +370(5)2330987 eMail: sigitas.tumkevicius@chf.vu.lt

,

Grazina Petraityte

Vilnius University, Department of Organic Chemistry, Vilnius 03225, Lithuania, Fax: +370(5)2330987 eMail: sigitas.tumkevicius@chf.vu.lt

,

Sigitas Tumkevicius*

Vilnius University, Department of Organic Chemistry, Vilnius 03225, Lithuania, Fax: +370(5)2330987 eMail: sigitas.tumkevicius@chf.vu.lt

› Institutsangaben

Abstract

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Abstract

An efficient method for the synthesis of 4-amino-5-(arylaminomethyl)-2-(methylthio)furo[2,3-d]pyrimidines via the Mitsunobu reaction of 4-amino-5-(hydroxymethyl)-2-(methylthio)furo[2,3-d]pyrimidine with N-mesyl- and N-nosylarylamines, and subsequent removal of the mesyl and nosyl groups, has been developed. The influence of substituents in the arylamine moiety on the Mitsunobu reaction was investigated. An unexpected nucleophilic substitution of a nitro group in the reaction of N-({4-amino-2-(methylsulfonyl)furo[2,3-d]pyrimidin-5-yl}methyl)-4-nitro-N-phenylbenzenesulfonamide with sodium methoxide was observed.

Key words

alkylation - sulfonamides - heterocycles - oxidation - nucleophilic aromatic substitution

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Referenzen

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