78030-76-9

Upstream product

• 78030-58-7 7-benzyl-N⁶-methoxy-9-methyladeninium bromide 
• 78030-58-7 7-benzyl-N⁶-methoxy-9-methyladeninium bromide 
• 78030-61-2 7-benzyl-N⁶-benzyloxy-9-methyladeninium bromide 
• 78030-61-2 7-benzyl-N⁶-benzyloxy-9-methyladeninium bromide 
• 100-39-0 benzyl bromide 
• 33174-54-8 5-formamido-N'-methoxy-1-methyl-1H-imidazole-4-carboxamidine 

Downstream Products

• 79831-22-4 7-Benzyl-N⁶-methyladenine 

Relevant academic research and scientific papers

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

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

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)