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Synthesis 2010(14): 2383-2392  
DOI: 10.1055/s-0029-1220009
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Highly Efficient Method for the N-Alkylation of Aminopyrazines: Synthesis of Hydrophilic Red Fluorescent Dyes

Amruta R. Poreddy*, Bethel Asmelash, William L. Neumann¹, Richard B. Dorshow
Covidien Pharmaceuticals, 675 McDonnell Boulevard, Hazelwood, MO 63042, USA
Fax: +1(314)6548900; e-Mail: amruta.poreddy@covidien.com;
Further Information

Publication History

Received 12 February 2010
Publication Date:
20 May 2010 (online)

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Abstract

A robust and scalable method was developed for the synthesis of N,N′-dialkylated aminopyrazines by a reductive amination route. These new fluorescent pyrazine analogues were shown to absorb and emit light at relatively long wavelengths (˜50 nm) compared to the corresponding diaminopyrazines. The utility of these compounds was demonstrated by the synthesis of hydrophilic fluorescent probes with potential diagnostic applications.

Key words

GFR - renal function - pyrazine - fluorescence - reductive amination

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1

New address: Department of Pharmaceutical Sciences, Southern Illinois University, 220 University Park Drive, Edwardsville, IL 62026, USA.

21

PEG-reagent is discrete, i.e., monodisperse and was purchased from Quanta BioDesign, Ltd., Powell, Ohio.

23

Analytical sample was prepared by filtering through a plug of silica gel using CHCl3-MeOH (19:1, v/v) as eluent.