15837-10-2

Basic information

• Product Name: 7H-Purine, 7,8-dimethyl- (9CI)
• Synonyms: 7H-Purine, 7,8-dimethyl- (9CI)
• CAS NO: 15837-10-2
• Molecular Formula: C₇H₈N₄
• Molecular Weight: 148.16522
• Product Categories: PYRIMIDINE
• Mol File: 15837-10-2.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 7H-Purine, 7,8-dimethyl- (9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 7H-Purine, 7,8-dimethyl- (9CI)(15837-10-2)
• EPA Substance Registry System: 7H-Purine, 7,8-dimethyl- (9CI)(15837-10-2)

Safety Data

• Hazardous Substances Data: 15837-10-2(Hazardous Substances Data)

Upstream product

• 77287-34-4 formamide 
• 188710-70-5 4-amino-1,2-dimethylimidazole-5-carbaldehyde 
• 108-24-7 acetic anhydride 
• 3059-67-4 N⁵-methyl-pyrimidine-4,5-diamine 
• 18346-04-8 7-methylpurine 

Relevant articles and documents

8-Purinyl versus 2-Benzimidazolyl Carbanions: Charge Demands of the Heterocycles and Ligand Properties of the Bis(heteroaryl)methanes

Two new purinyl derivatives, 8-benzyl-7-methylpurine (8) and bis(7-methylpurin-8-yl)methane (9), have been synthesized and their corresponding carbanions investigated in DMSO. The application of our previously proposed π-charge/shift relationships to the 13C and 15N shifts of the carbanions has made it possible to map π-charges and obtain the values of the charge demand of the heterocyclic rings, a resonance index of the π-electron-withdrawing power of the substituent. The charge demand of the 7-methylpurin-8-yl substituent is found to be the highest among the previously investigated azinyl and azolyl substituents and is comparable with that of the strongest classical electron-withdrawing functions. The replacement of the fused benzene ring in the benzimidazolyl substituent by a pyrimidine ring containing the nitrogen atoms in appropriate positions causes a considerable increase in the electron-withdrawing capacity of the heterocycle. Spectroscopic and reactivity data confirm the strong electron-withdrawing nature of the purinyl ring. The 13C NMR spectrum shows the existence of the carbanions of both purinyl derivatives as a mixture of geometric isomers, a consequence of the high double-bond character along the bond linking the carbanionic carbon to C(8) of the purinyl ring. Bis(7-methylpurin-8-yl)methane can be easily converted to its stable NH tautomer by means of basic catalysis. It behaves as an "active methylene" compound giving high-yield condensations with electrophiles. Finally, unlike the corresponding benzimidazol-2-yl derivative, bis(7-methylpurin-8-yl)methane reacts with metal acetates to give neutral methanates [ML2] (M = Zn, Cu, Co; LH = bis(7-methylpurin-8-yl)methane), where the ligand is present as an anionic system. On the basis of this and previous data, it is concluded that charge demand plays a strategic role in obtaining stable chelates of this sort.