5451-41-2

Upstream product

• 109-73-9 N-butylamine 
• 50-66-8 6-(methylthio)-1H-purine 
• 68-94-0 1,7-dihydro-6H-purin-6-one 
• 50-44-2 6H-purine-6-thione 
• 10557-57-0 propylmagnesium iodide 
• 111098-24-9 Benzotriazol-1-ylmethyl-(9H-purin-6-yl)-amine 
• 19769-32-5 6-methylsulfonylpurine 
• 87-42-3 6-chloropurine 
• 50-66-8 6-methylthiopurine 
• 1229622-73-4 C₃₃H₃₅N₅O₂ 
• 66224-66-6 adenine 

Downstream Products

• 109-73-9 N-butylamine 
• 68-94-0 hypoxanthine 
• 23096-10-8 N₆-butyladenosine 

Relevant academic research and scientific papers

COMPOSITIONS AND METHODS USING THE SAME FOR TREATMENT OF NEURODEGENERATIVE AND MITOCHONDRIAL DISEASE

The present disclosure is directed, in part, to compounds, or pharmaceutically acceptable salts thereof, for the treatment and/or prevention of neurodegenerative disease and/or mitchonodrial disease including Parkinson's disease and Leigh's disease.

Convenient and efficient syntheses of N6-and N 4-substituted adenines and cytosines and their 2-deoxyribosides

Convenient and efficient methods of the synthesis of N6-and N4-substituted derivatives of adenine and cytosine and their 2-deoxyribosides were developed. The reactions of either unprotected nucleobases (adenine, cytosine) or unprotected 2-deoxyribosides with aryl or alkyl aldehydes give corresponding Schiff bases that can be reduced to the target title compounds with high overall yields. In the case of aryl aldehydes the imine derivatives are obtained in the presence of methoxides in methanol and reduced with sodium borohydride. The corresponding reactions with alkyl aldehydes require the use of acetic acid and borane dimethyl sulfide complex instead.

Synthesis and antiviral evaluation of bis(POM) prodrugs of (E)-[4′-phosphono-but-2′-en-1′-yl]purine nucleosides

Seventeen hitherto unknown bis(POM) prodrugs of novel (E)-[4′- phosphono-but-2′-en-1′-yl]purine nucleosides were prepared in a straight approach and at good yields. Those compounds were synthesized by the reaction of purine nucleobases directly with the p

Regioselective alkylation of the exocyclic nitrogen of adenine and adenosine by the Mitsunobu reaction

A novel synthetic route to N6-substitution of adenine is presented, employing the Mitsunobu reaction as the key step. A range of primary and secondary alcohols all coupled in very good to excellent yields within 30 min at 45 °C, offering a milder alternative to the traditional nucleophilic aromatic substitution of 6-chloropurine. The utility of this protocol is further demonstrated by its application to the syntheses of N6,N9-di-substituted adenines, including the potent and selective A1 adenosine receptor agonist N6-cyclopentyladenosine.

The scope and mechanism of phosphonium-mediated SNAr reactions in heterocyclic amides and ureas

(Chemical Equation Presented) An efficient "one-step" synthesis of cyclic amidines and guanidines has been developed. Treatment of cyclic amides and ureas with benzotriazol-l-yloxytris(dimethylamino)phosphonium hexafluorophosphate (BOP), base, and nitrogen nucleophiles leads to the formation of the corresponding cyclic amidines and guanidines, typically in good to excellent yields. This method has also been used to prepare heteroaryl ethers and thioethers using phenol and thiophenol nucleophiles. Time course NMR and HPLC-MS studies have facilitated explicit characterization of the proposed intermediates (the phosphonium salt and HOBt adduct); the data reveal a stepwise reaction pathway.

An efficient synthesis of substituted cytosines and purines under focused microwave irradiation

A rapid nucleophilic displacement reaction of 6-chloropurine, 2-amino-6-chloropurine and 5-bromocytosine with various nucleophiles under focused microwave irradiation is described. Using this method, the desired products were obtained with the yields up to 99% in?a?short reaction time.

An efficient direct amination of cyclic amides and cyclic ureas

An efficient one-step amination of cyclic amides and ureas has been developed. Treatment of cyclic amides and cyclic ureas with BOP in the presence of DBU in various solvents led to the formation of cyclic amidines and cyclic guanidines in good to excellent yields. Concise syntheses of biologically intriguing kinetin and potent kinase inhibitor olomoucin were thus achieved in just one and two steps, respectively.

Synthesis of 6-alkyl- and arylamino-9-(tetrahydro-2-pyranyl)purines via 6-methylsulfonylpurine

A series of six potential plant hormones, 6-alky- and arylamino-9- (tetrahydro-2-pyranyl)purines were prepared in three steps in 35 to 45% overall yield from 6-methylthiopurine via 6-methylsulfonylpurine.

The Chemistry of N-Substituted Benzotriazoles. Part 4. A Novel and Versatile Method for the Mono-N-alkylation of Aromatic and Heteroaromatic Amines

Mono-N-alkylation of aromatic and heteroaromatic amines is achieved in high yield by NaBH4 reduction of the adducts formed from benzotriazole, aliphatic aldehydes and the amines.Reaction of the same adducts with Grignard reagents gives N-(secondary alkyl)arylamines.Carboxy groups need no protection and nitro groups are unaffected.Adenine is mono-N-alkylated in high yield.