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4-Chloro-2-(Methylsulfonyl)pyrimidine - CAS 97229-11-3

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Category
Main Product
Product Name
4-Chloro-2-(Methylsulfonyl)pyrimidine
Catalog Number
97229-11-3
Synonyms
4-CHLORO-2-METHANESULFONYL-PYRIMIDINE;4-Chloro-2-(methylsulfonyl)pyrimidine;4-Chloro-2-(methylsulfonyl)pyrimidine ,98%
CAS Number
97229-11-3
Molecular Weight
192.62
Molecular Formula
C5H5N2ClS
COA
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MSDS
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Structure
CAS 97229-11-3 4-Chloro-2-(Methylsulfonyl)pyrimidine
Specification
Purity
95%
Boiling Point
371.2ºC at 760 mmHg
Melting Point
87-89ºC
Density
1.486
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Reference Reading
1.Synthesis and antiviral activity of certain 4-substituted and 2,4-disubstituted 7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidines.
Saxena NK1, Hagenow BM, Genzlinger G, Turk SR, Drach JC, Townsend LB. J Med Chem. 1988 Aug;31(8):1501-6.
Treatment of the sodium salt of 4-chloro-2-(methylthio)pyrrolo[2,3-d]pyrimidine (2) with (2-acetoxyethoxy)methyl bromide (3) has provided 4-chloro-2-(methylthio)-7[(2-acetoxyethoxy)methyl]pyrrolo[2,3- d]pyrimidine (4). Ammonolysis of 4 at room temperature gave 4-chloro-2-(methylthio)-7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3- d]pyrimidine (5). However, ammonolysis of 5 at 130 degrees C furnished 4-amino-2-(methylthio)-7-[(2-hydroxyethoxy)methyl]-pyrrolo[2,3- d]pyrimidine (6), which on desulfurization with Raney Ni yielded 4-amino-7-[(2-hydroxyethoxy)-methyl]pyrrolo[2,3-d]pyrimidine (7) (acyclic analogue of tubercidin). The oxidation of 6 with m-chloroperbenzoic acid provided the sulfone derivative 8. A nucleophilic displacement of the 2-methylsulfonyl group from 8 with methoxide anion provided 4-amino-2-methoxy-7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine (9). Demethylation of 9 with iodotrimethylsilane gave 4-amino-2-hydroxy-7-[(2-hydroxyethoxy)methyl]pyrrolo[2,3-d]pyrimidine (10).
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