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Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 3

โœ Scribed by Virginie Brun; Michel Legraverend; David S Grierson

Publisher
Elsevier Science
Year
2001
Tongue
French
Weight
102 KB
Volume
42
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

Experiments to effect Sonogashira (Ph 3 P) 2 Cl 2 Pd-CuI-based coupling of 3-methylpentyn-3-ol at C-2 of a 2-iodo-6-thiopurine derivative, bound via the sulfur atom to a Merrifield resin failed. In contrast, the analogous reaction with Pd(dppe)Cl 2 and trans-di(m-acetato)bis[o-(di-o-tolylphosphino)benzyl]dipalladium catalysts were successful (20-25%), indicating that (Ph 3 P) 2 Pd(0) loses its ligands irreversibly on contact with the resin bound purine. The coupling yield was improved considerably (58%) using a Merrifield resin in which a valeric acid linker is interposed between the purine and the resin.

๐Ÿ“œ SIMILAR VOLUMES

Cyclin-dependent kinase (CDK) inhibitors
Cyclin-dependent kinase (CDK) inhibitors: development of a general strategy for the construction of 2,6,9-trisubstituted purine libraries. Part 1
โœ Virginie Brun; Michel Legraverend; David S Grierson ๐Ÿ“‚ Article ๐Ÿ“… 2001 ๐Ÿ› Elsevier Science ๐ŸŒ French โš– 123 KB

To validate a proposed solid support synthesis strategy for the construction of 2,6,9-trisubstituted purine based CDK inhibitors, the N-9 THP protected 6-benzylthio-2-iodopurine 11 was reacted with piperidine-2-methanol to give 12. Alternatively, intermediate 11 was converted to the C-2 acetylenyl s