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Synthesis and Crystal Structures of Two 9‐(2‐Bromoethyl)‐Substituted 7‐Deazapurines
Author(s) -
Asaftei Simona,
Reichelt Martin,
Reuter Hans,
Rosemeyer Helmut
Publication year - 2009
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.200900145
Subject(s) - chemistry , substituent , ring (chemistry) , pyrimidine , nucleobase , amine gas treating , alkylation , crystal structure , amidine , stereochemistry , ion , medicinal chemistry , crystallography , organic chemistry , dna , catalysis , biochemistry
The 7‐(2‐bromoethyl) derivatives, 2a and 2b , of 4‐chloro‐7 H ‐pyrrolo[2,3‐ d ]pyrimidine ( 1a ) and 4‐chloro‐7 H ‐pyrrolo[2,3‐ d ]pyrimidin‐2‐amine ( 1b ) were synthesized by nucleobase anion alkylation (NaH, DMF) and crystallized. X‐Ray analyses of both compounds were performed, and they revealed significantly different positioning of the side chain relative to the heterocyclic ring, depending on the substituent (H or NH 2 ) at C(2).