79831-22-4

Basic information

• Product Name: 7-Benzyl-N⁶-methyladenine
• Synonyms: 7-Benzyl-N⁶-methyladenine
• CAS NO: 79831-22-4
• Molecular Weight: 239.28
• Mol File: 79831-22-4.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 7-Benzyl-N⁶-methyladenine(CAS DataBase Reference)
• NIST Chemistry Reference: 7-Benzyl-N⁶-methyladenine(79831-22-4)
• EPA Substance Registry System: 7-Benzyl-N⁶-methyladenine(79831-22-4)

Safety Data

• Hazardous Substances Data: 79831-22-4(Hazardous Substances Data)

Upstream product

• 33174-54-8 5-formamido-N'-methoxy-1-methyl-1H-imidazole-4-carboxamidine 
• 100-39-0 benzyl bromide 
• 78030-58-7 7-benzyl-N⁶-methoxy-9-methyladeninium bromide 
• 78030-76-9 7-benzyl-9-methyladeninium bromide 

Relevant articles and documents

Purines. LX. Dimroth rearrangement and concomitant hydrolytic deamination of 7-alkyl-1-methyladenines

The Dimroth rearrangement of 7-alkyl-1-methyladenines (8) to produce 7- alkyl-N6-methyladenines (9) (63-72% yield) has been found to be accompanied with unusual hydrolytic deaminations to give 7-alkyl-1-methyl-hypoxanthines (10) (1-3.5%) and/or 7-alkylhypoxanthines (11) (12-22%), when effected in boiling H2O for 4-70 h. Probable pathways leading to these by-products are proposed.

Purines. XXX. Ring Fission of 3,7-Dialkyladenines by Alkaline Hydrolysis

On treatment with boiling 1 N aqueous NaOH for 2 h, 3,7-dialkyladenine salts (7: R1, R2= Me, Et, or PhCH2; X= Br, I, or ClO4) gave 1-alkyl-4-(N-alkylamino)-1H-imidazole-5-carboxamides (8), 1-alkyl-4-amino-1H-imidazole-5-carboxamides (11), and N6,7-dialkyladenines (14) in 33-59 percent, 2-10 percent, and 2-5 percent yields, respectively.Under slightly milder reaction conditions, 3,7-dimethyladenine hydriodide (7a: X= I) afforded 1-methyl-4-(N-methylamino)-1H-imidazole-5-carboxamide (8a) together with 3,7-dimethylhypoxanthine (2a) as a by-product; 7-benzyl-3-methyladenine hydrobromide (7c: X= Br) furnished a small amount of 1-benzyl-4-(N-methylamino)-1H-imidazole-5-carboxamidine (5c) besides 1-benzyl-4-(N-methylamino)-1H-imidazole-5-carboxamide (8c), 1-benzyl-4-amino-1H-imidazole-5-carboxamide (11c), and 7-benzyl-N6-methyladenine (14c).These results are best interpreted in terms of pathways involving hydrolytic deamination, ring fission in the pyrimidine and imidazole moieties, cyclization, and Dimroth rearrangement.The instability of 7a (X= I) in aqueous alkali was compared with that of the four possible Nx,9-dimethyl isomers, and the relative ease with which the adenine ring underwent hydrolytic ring fission was found to decrease in the order 3,9- (17) >7,9- (18) >1,9- (19) >3,7- (7a) >>N6,9-dimethyl isomer (20).Keywords - 3,7-dialkyladenine alkaline hydrolysis; ring fission; deamination; rearrangement; 1-alkyl-4-(N-alkylamino)-1H-imidazole-5-carboxamide; 1-alkyl-4-amino-1H-imidazole-5-carboxamide; N6,7-dialkyladenine