90801-87-9

Basic information

• Product Name: 1H-Imidazole-4-carboxamide,5-(methylamino)-(9CI)
• Synonyms: 1H-Imidazole-4-carboxamide,5-(methylamino)-(9CI);5-(methylamino)-1H-imidazole-4-carboxamide;Temozolomide Impurity E
• CAS NO: 90801-87-9
• Molecular Formula: C5H8N4O
• Molecular Weight: 140.14322
• Product Categories: AMIDE
• Mol File: 90801-87-9.mol
• Article Data: 1

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 1H-Imidazole-4-carboxamide,5-(methylamino)-(9CI)(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Imidazole-4-carboxamide,5-(methylamino)-(9CI)(90801-87-9)
• EPA Substance Registry System: 1H-Imidazole-4-carboxamide,5-(methylamino)-(9CI)(90801-87-9)

Safety Data

• Hazardous Substances Data: 90801-87-9(Hazardous Substances Data)

Usage

Parent compound

Imidazole, a five-membered heterocyclic ring with three carbon atoms and two nitrogen atoms.

Attached groups

A carboxamide group and a methylamino group.

Potential applications

Pharmaceutical and chemical research, as a building block for the synthesis of various drugs and bioactive compounds.

Drug development potential

The presence of the methylamino group makes it a candidate for drug development and pharmaceutical applications.

Value in research

Its structure and properties make it a valuable compound for further study and potential applications in various industries.

Upstream product

• 5142-23-4 3-methyladenine 

Downstream Products

• 93703-24-3 3-methyl-8-bromoxanthine 
• 666816-98-4 8-bromo-7-(but2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6–dione 
• 853029-57-9 2-bromo-1-(but-2-ynyl)-4-methyl-6-((4-methylquinazolin-2-yl)methyl)-1H-imidazo[4,5-b]pyridine-5,7-(4H,6H)-dione 
• 1076-22-8 3-methylxanthine 

Relevant articles and documents

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