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Molbank 2007, 2007(4), M555; doi:10.3390/M555

Synthesis of 3-(4-Amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propanoic acid – A Functionalized Base Derivative of the Nucleoside Antibiotic Tubercidin

Organische Chemie I – Bioorganische Chemie, Institut für Chemie, Fachbereich Biologie/Chemie, Universität Osnabrück, Barbarastr. 7, D-49069 Osnabrück, Germany
Received: 5 June 2007 / Accepted: 24 August 2007 / Published: 27 August 2007
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Abstract

Regioselective N-alkylation of 4-chloro-2-(methylthio)-7H-pyrrolo[2,3-d]pyrimidine (1) with ethyl 3-bromopropionate under liquid-liquid phase transfer reaction conditions and further saponification of the ester function under formation of compound 3b is described. Subsequent SNAr substitution of the 4-chloro substituent by an amino function and reductive removal of the 2-methylthio group of 3b gives, via 4a, the title compound 4b.
Keywords: 7-Deazaadenine; Tubercidin; Functionalization 7-Deazaadenine; Tubercidin; Functionalization
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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MDPI and ACS Style

Rosemeyer, H. Synthesis of 3-(4-Amino-7H-pyrrolo[2,3-d]pyrimidin-7-yl)propanoic acid – A Functionalized Base Derivative of the Nucleoside Antibiotic Tubercidin. Molbank 2007, 2007, M555.

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