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

doi:10.3390/M555

This article is

freely available
re-usable

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

Short Note

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

Helmut Rosemeyer

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

Download PDF Full-Text [136 KB, uploaded 24 February 2009 08:52 CET]

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 S_NAr 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

Supplementary Files

Supplementary File 1:
m555.mol 3D structure (MOL, 2 KB) Display in MOL Viewer
3D structure generated by CORINA by Molecular Networks.
Supplementary File 2:
m555.mol (MOL, 2 KB) Display in MOL Viewer

Article Statistics

Click here to load and display the download statistics.

Cite This Article

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.

AMA 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(4):M555.

Chicago/Turabian Style

Rosemeyer, Helmut. 2007. "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, no. 4: M555.

Molbank EISSN 1422-8599 Published by MDPI Publishing, Basel, Switzerland RSS E-Mail Table of Contents Alert