218431-10-8

Basic information

• Product Name: 6-Chloro-8-iodo-9-(tetrahydro-pyran-2-yl)-9H-purine
• Synonyms: 6-Chloro-8-iodo-9-(tetrahydro-pyran-2-yl)-9H-purine
• CAS NO: 218431-10-8
• Molecular Formula: C₁₀H₁₀ClIN₄O
• Molecular Weight: 364.57007
• Mol File: 218431-10-8.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 6-Chloro-8-iodo-9-(tetrahydro-pyran-2-yl)-9H-purine(CAS DataBase Reference)
• NIST Chemistry Reference: 6-Chloro-8-iodo-9-(tetrahydro-pyran-2-yl)-9H-purine(218431-10-8)
• EPA Substance Registry System: 6-Chloro-8-iodo-9-(tetrahydro-pyran-2-yl)-9H-purine(218431-10-8)

Safety Data

• Hazardous Substances Data: 218431-10-8(Hazardous Substances Data)

Upstream product

• 142-68-7 TETRAHYDROPYRANE 
• 87-42-3 6-chloropurine 
• 7306-68-5 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 

Downstream Products

• 1262785-84-1 6-chloro-8-phenyl-9-(tetrahydro-2H-pyran-2-yl)-9H-purine 
• 1386995-02-3 C₁₇H₁₆ClN₅O₂ 

Relevant articles and documents

Design, synthesis, and anticancer activity of C8-substituted-4′-thionucleosides as potential HSP90 inhibitors

A series of C8-substituted-4′-thioadenosine analogs 3a–3g, 15, and 17 and their truncated derivatives 4a–4j, 23–25, and 27 have been successfully synthesized from D-ribose and D-mannose, respectively, employing Pummerer type or Vorbrüggen condensation reactions and the functionalization at the C8-position of nucleobase via Stille coupling or nucleophilic aromatic substitution reactions as key steps. All the synthesized compounds were assayed for their HSP90 inhibitory activity, but they were found to be inactive up to 100 μM. However, the 8-iodo derivatives 15, 17, and 27 exhibited potent anticancer activity, indicating that different mechanism of action might be involved in their biological activity.

Regioselective functionalization of purine derivatives at positions 8 and 6 using hindered TMP-amide bases of Zn and Mg

A broad range of purine derivatives were efficiently metalated at positions 8 and 6 using TMP-amide bases. This provided polysubstituted purines in good to very good yields after subsequent trapping of the zinc or magnesium intermediates with various elec

Regioselective Sonogashira cross-coupling reactions of 6-chloro-2,8-diiodo- 9-THP-9H-purine with alkyne derivatives

Lithiation of 6-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purine with LiTMP, gave access to 6-chloro-2,8-dihalogenated purine derivatives. In particular, the 6-chloro-2,8-diiodopurine derivative is an interesting new intermediate which gave regioselectively various 2-alkynylated compounds or 2,8-dialkynylated purines by using an excess of alkyne.

Synthesis of 8-halopurines by reaction of lithiated purines with appropriate halogen donors

Purines lithiated in the 8-position, can be trapped with hexachloroethane, dibromotetrachloroethane, cyanogen bromide and cyanogen iodide, to give a variety of 8-halopurines in excellent yields.