98601-03-7

Basic information

• Product Name: (6Z)-6-imino-1,9-dimethyl-1,6,7,9-tetrahydro-8H-purin-8-one
• CAS NO: 98601-03-7
• Molecular Formula: C₇H₉N₅O
• Molecular Weight: 179.1793
• Mol File: 98601-03-7.mol

Chemical Properties

• Density: 1.6g/cm³
• Refractive Index: 1.764
• CAS DataBase Reference: (6Z)-6-imino-1,9-dimethyl-1,6,7,9-tetrahydro-8H-purin-8-one(CAS DataBase Reference)
• NIST Chemistry Reference: (6Z)-6-imino-1,9-dimethyl-1,6,7,9-tetrahydro-8H-purin-8-one(98601-03-7)
• EPA Substance Registry System: (6Z)-6-imino-1,9-dimethyl-1,6,7,9-tetrahydro-8H-purin-8-one(98601-03-7)

Safety Data

• Hazardous Substances Data: 98601-03-7(Hazardous Substances Data)

Upstream product

• 119138-92-0 6-Amino-9-methyl-7H-purin-8(9H)-one 
• 130999-35-8 8-bromo-6-imino-1,9-dimethylpurine 
• 64-19-7 acetic acid 
• 133329-70-1 1,6,7,9-tetrahydro-1,9-dimethyl-6-<(phenylmethyl)imino>-8H-purin-8-one hydrochloride 
• 127-09-3 sodium acetate 
• 133329-69-8 1,6,7,9-tetrahydro-1,9-dimethyl-6-<(phenylmethyl)imino>-8H-purin-8-one hydriodide 
• 119138-89-5 8-bromo-6-imino-1,9-dimethylpurine hydroiodide 
• 700-00-5 3-methyladenine 
• 56489-40-8 8-bromo-9-methyl-9H-purin-6-amine 
• 74-88-4 methyl iodide 
• 133329-67-6 7,9-dihydro-9-methyl-6-<(phenylmethyl)amino>-8H-purin-8-one 
• 133329-66-5 1-Benzyl-6-imino-9-methyl-1,6,7,9-tetrahydro-purin-8-one 

Relevant articles and documents

Purines. LVII. Regioselective alkylation of N6,9-disubstituted 8- oxoadenines: Syntheses of the sea anemone purine caissarone and some positional isomers and analogues

The first total synthesis of caissarone hydrochloride (1), a constituent of the sea anemone Bunodosoma caissarum, has been accomplished via a two- step route starting from N6,9-dimethyl-8-oxoadenine (3), which is obtainable from 9-methyladenine (5) through a four-step route. The key step in the synthesis is the regioselective methylation of 3 at N(3), which has been designed on the basis of a methylation study of N6-benzyl-9-methyl-8- oxoadenine (11). Some positional isomers (19, 24, and 31) and analogues (8, 26, and 32) of 1 have also been synthesized. A 1H-NMR spectroscopic study has suggested that the free base (23) of caissarone is capable of forming a hetero-base pair (such as 41) with 2',3',5'-tri-O-acetylguanosine (40) in Me2SO-d6.

SYNTHESIS OF THE SEA ANEMONE PURINE CAISSARONE

On the basis of a methylation of N6-benzyl-9-methyl-8-oxoadenine (8), the first synthesis of caissarone hydrochloride (1) has been achieved via a two-step route including methylation of N6-methyl analogue (3).

SYNTHESIS OF 6-IMINO-1,9-DIMETHYL-8-OXOPURINE, A CONSTITUENT OF THE MARINE SPONGE HYMENIACIDON SANGUINEA GRANT

The marine 8-oxopurine I was synthesized from 8-bromo-9-methyladenine (VI) through the intermediates VII*HI and VII or, more effectively, through 6-amino-9-methyl-8-oxopurine (VIII).The N6-acetyl derivative II and the rearranged isomer X were also prepared.