133329-66-5

Upstream product

• 100-39-0 benzyl bromide 
• 198023-22-2 6-Amino-9-methyl-1-oxy-7,9-dihydro-purin-8-one 
• 119138-92-0 6-Amino-9-methyl-7H-purin-8(9H)-one 
• 198023-21-1 2-Bromo-N-methoxy-1-methyl-5-methylamino-1H-imidazole-4-carboxamidine 
• 70276-42-5 5-(formyl-methyl-amino)-N-methoxy-1-methyl-1H-imidazole-4-carboximidic acid amide 
• 198023-25-5 6-Amino-7-benzyl-9-methyl-7,9-dihydro-purin-8-one 
• 198023-20-0 2-Bromo-5-(formyl-methyl-amino)-N-methoxy-1-methyl-1H-imidazole-4-carboxamidine 

Downstream Products

• 98601-03-7 6-imino-1,9-dimethyl-8-oxopurine 
• 133329-71-2 6-[(Z)-Benzylimino]-3,9-dimethyl-3,6,7,9-tetrahydro-purin-8-one; hydrochloride 
• 133329-68-7 6-[(Z)-Benzylimino]-3,9-dimethyl-3,6,7,9-tetrahydro-purin-8-one; hydriodide 
• 133329-70-1 1,6,7,9-tetrahydro-1,9-dimethyl-6-<(phenylmethyl)imino>-8H-purin-8-one hydrochloride 
• 133329-69-8 1,6,7,9-tetrahydro-1,9-dimethyl-6-<(phenylmethyl)imino>-8H-purin-8-one hydriodide 

Relevant academic research and scientific papers

Purines. LXXVII. An alternative synthesis of N6-demethylcaissarone from 9-methyl-8-oxoadenine by regioselective N(3)-methylation: Utilization of the N(7)-benzyl and N(1)-benzyloxy groups as control synthons

An alternative synthesis of 3,9-dimethyl-8-oxoadenine (N6- demethylcaissarone) hydrochloride (5a-HCI) starting from 9-methyl-8- oxoadenine (17) is described. The synthesis proceeded through N(7)- benzylation, N(1)-oxidation, and O-benzylation to afford the 1-benzyloxy derivative 25, which afforded the ring-opened formamide derivative 26 on treatment with dilute aqueous NaOH. Methylation of the monocycle 26 with MeI in the presence of K2CO3, followed by acid-catalyzed cyclization and subsequent catalytic hydrogenolysis afforded 5a·HCl. The key intermediate 25 was alternatively prepared from 17 by N-oxidation and subsequent O,N(7)- dibenzylation with PhCH2Br in the presence of K2CO3.

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).