56046-26-5

Upstream product

• 66224-66-6 adenine 
• 105-13-5 4-Methoxybenzyl alcohol 
• 73-24-5 7H-purin-6-ylamine 
• 824-94-2 p-methoxybenzyl chloride 

Downstream Products

• 1197007-70-7 C₂₀H₁₉N₅O 
• 1197007-69-4 C₂₀H₁₉N₅O 
• 1197007-72-9 C₂₀H₁₈N₆O₂ 
• 1197007-75-2 C₁₈H₁₆N₆O 

Relevant academic research and scientific papers

One-pot synthesis of N-alkyl purine and pyrimidine derivatives from alcohols using TsIm: a rapid entry into carboacyclic nucleoside synthesis

A convenient and efficient one-pot N-alkylation of nucleobases from alcohols using N-(p-toluenesulfonyl)imidazole (TsIm) is described. In this method, treatment of alcohols with a mixture of purine or pyrimidine nucleobase, TsIm, K2CO3, and triethylamine in refluxing DMF regioselectively furnishes the corresponding N-alkyl nucleobases in good yields. This methodology is highly efficient for various structurally diverse primary alcohols.

One-pot protocol for N-alkylation of purine, pyrimidine and azole derivatives via alcohols using Ph3P/I2: simple route for carboacyclic nucleoside synthesis

A simple and efficient synthetic protocol for the one-pot N-alkylation of nucleobases and their related N-heterocycles via alcohols utilizing the combination of PPh3and I2is reported. In this protocol purine, pyrimidine and azole derivatives underwent the N-alkylation reaction with diverse primary alcohols using Ph3P/I2in the presence of Et3N-K2CO3in anhydrous DMF to give the N-alkyl adducts (carboacyclic nucleosides) in good yields (up to 90%). The influence of some parameters in this reaction including type of solvent, base, reagents and temperature was discussed. In addition, this protocol has proved the favorable selectivity towards primary hydroxyl versus secondary hydroxyl group in diols.

Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohols in bmim[Br]: A rapid route to access acyclic nucleosides

Highly efficient protocol for one-pot N-alkylation of nucleobases using alcohol in ionic liquid media as a straightforward route to access acyclic nucleoside was described. In this protocol purine, pyrimidine as well as azole derivatives underwent the N-a

One-pot synthesis of n-alkyl purine, pyrimidine and azole derivatives from alcohols using ph3p/ccl4: A rapid route to carboacyclic nucleoside synthesis

A facile and efficient method for one-pot N-alkylation of nucleobases and azole derivatives from alcohols using triphenylphosphine in carbon tetrachloride is described. In this method, treatment of alcohols with a mixture of triphenylphosphine, carbon tetrachloride, nucleobase or azole derivatives and potassium carbonate in the presence of catalytic amounts of tetra-n- butylammonium iodide (TBAI) in refluxing N,N-dimethylformamide, furnishes the corresponding N-alkyl derivatives in good yields. This methodology is highly efficient for various structurally diverse primary alcohols and also useful for N-alkylation of other N-heterocycles containing an acidic N-H bond.

Heterocyclic Ambident Nucleophiles. III* The Alkylation of Sodium Adenide

The alkylation of sodium adenide in HCONMe2 (30 deg) with various alkylating agents was analysed by 1H n.m.r. spectroscopy.Widely varying N3:N7:N9 alkylation patterns were observed, depending on the alkylating agent.These patterns are interpreted in terms of the electrostatic, thermodynamic and steric factors involved in the different SN2 transition states appropriate to each alkylating agent.Hydrogen bonding association between the 6-amino group and certain carbonyl containing alkylating agents is proposed to explain the enhancedN7-alkylation in some cases.Support for this latter proposal was obtain from a comparison of the adenine alkylation results with the corresponding alkylation patterns of 6-pivaloylamino- and 6-chloro-purine.