78030-58-7

Upstream product

• 13300-29-3 N⁶-methoxy-9-methyladenine 
• 100-39-0 benzyl bromide 
• 33174-54-8 5-formamido-N'-methoxy-1-methyl-1H-imidazole-4-carboxamidine 

Downstream Products

• 78030-76-9 7-benzyl-9-methyladeninium bromide 
• 79831-22-4 7-Benzyl-N⁶-methyladenine 

Relevant academic research and scientific papers

Synthetic studies directed towards agelasine analogs - Synthesis, tautomerism, and alkylation of 2-substituted N-methoxy-9-methyl-9H-purin-6- amines

N-Methoxy-9-methyl-9H-purin-6-amines, carrying various substituents in the 2 positions, were synthesized by the N-methylation of known 6-chloropurines, followed by a displacement of the chlorine. Great variations in the amino/imino tautomer ratio among the compounds studied were observed. The tautomers were identified by NMR methods. Treatment of N-methoxy-9-methyl-9H-purin-6-amines carrying alkyl, alkoxy, or amino substituents in the 2 position with benzyl bromide resulted in a mixture of N-7- and N6-benzylated compounds with the former as the major products. N-Methoxy-9-methyl-9H-purin-6-amines with strongly electronegative substituents at C-2 hardly reacted at all under the same set of reaction conditions. Wiley-VCH Verlag GmbH & Co. KGaA, 2008.

Purines. xxxviii. A general synthesis of 7,9-dialkyladeninium salts from 9-alkyladenines by regioselective alkylation: Utilization of an N6-alkoxy group as a control synthon

A detailed account is given of the general synthetic route to 7,9-dialkyladeninium salts (16 18) from N6-alkoxy-9-alkyladenines (type 5 or 11--13), readily obtainable from 9-alkyladenines in three steps involving N(1)-oxidation, O-alkylation, a

7,9-Dialkyladeninium salts. An alternative synthesis, ring opening, and rearrangement to N6,7-dialkyladenines

Alkylation of N1-alkoxy-1-alkyl-5-formamidoimidazole-4-carboxamidine (type I or II) (in the absence of any base) followed by hydrogenolysis of the N1-alkoxy group and cyclization (or vice versa) yielded the corresponding 7,9-dialkyladeninium salts (type VII), which readily rearranged to N6,7-dialkyladenines (type X) in boiling 1 N NaOH.Under milder basic conditions, VII underwent hydrolysis to produce 4-alkylamino-6-amino-5-formamidopyrimidines (VIII).The NaBH4 reduction of 7,9-dimethyladeninium iodide (VIIa, X=I) gave the 7,8-dihydro derivative (XI)

A GENERAL SYNTHESIS OF 7,9-DIALKYLADENINIUM SALTS

Alkylations of N6-methoxy-9-methyladenine (I) and 9-alkyl-N6-benzyloxyadenines (II-IV) with MeI, EtI, and PhCH2Br in N,N-dimethylacetamide yielded the corresponding 7-alkylated derivatives (X, XIV-XVI), together with small amounts of