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About This Item
Empirical Formula (Hill Notation):
C5H3ClN4
CAS Number:
Molecular Weight:
154.56
Beilstein/REAXYS Number:
5774
EC Number:
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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Quality Level
assay
≥99%
form
powder
mp
>300 °C (dec.) (lit.)
solubility
DMF: soluble 5%, clear, colorless to yellow
functional group
chloro
SMILES string
Clc1ncnc2[nH]cnc12
InChI
1S/C5H3ClN4/c6-4-3-5(9-1-7-3)10-2-8-4/h1-2H,(H,7,8,9,10)
InChI key
ZKBQDFAWXLTYKS-UHFFFAOYSA-N
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General description
The acid-catalyzed reaction of 6-chloropurine with 3,4-di-O-acetyl-D-xylal has been investigated.
Application
6-Chloropurine has been used in the preparation of 9-alkylpurines via alkylation with various substituted alkyl halides in DMSO. It was also used in the preparation of 6-succinoaminopurine.
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Heterocyclic N-glycosides-V: Synthesis of unsaturated N-glycosides from 6-chloropurine and derivatives of d-xylal and l-arabinal. A conformational NMR study.
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An efficient method for the synthesis of 6-alkyl or 6-aryl purines (nucleosides) was developed via nickel-catalyzed Negishi cross-couplings of 6-chloropurines and organozinc halides. The ligand-free process gave good to excellent isolated yields at room temperature.
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