55242-68-7

Upstream product

• 23043-88-1 7-ethyl-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 115377-55-4 1-ethyl-4-(N-methylamino)-1H-imidazole-5-carboxamide 
• 1076-22-8 3-methylxanthine 
• 75-03-6 ethyl iodide 

Downstream Products

• 139928-01-1 1-Benzyl-7-ethyl-3-methyl-3,7-dihydro-purine-2,6-dione 
• 55242-59-6 7-ethyl-3-methyl-1-(5-oxohexyl)-1H-purine-2,6(3H,7H)-dione 

Relevant academic research and scientific papers

Hydroxypurine compound and use thereof

The invention discloses a hydroxypurine compound and a use of the hydroxypurine compound as a PDE2 or TNFa inhibitor and concretely discloses a compound shown in the formula (I) and its tautomer or pharmaceutically acceptable salt.

Purines. XLIX. Synthesis and proton nuclear magnetic resonance study of 3,7-dialkylxanthines and 1,3,7-trialkylxanthines

A general synthetic route to 3,7-dialkylxanthines (type 9) from 3,7-dialkyladenines (6) [hence from 3- or 7-alkyladenines (11 or 10)] has been established. The route started with ethoxycarbonylation of 1-alkyl-4-(alkylamino)1H-imidazole-5-carboxamides (7), readily obtainable from 6 by alkaline hydrolysis, and proceeded through cyclization of the resulting carbamates (8) under alkaline conditions. Alkylation of 9 with alkyl halide in N,N-dimethylformamide in the presence of anhydrous K2CO3 extended the above synthetic route to the 1,3,7-trialkylxanthine level (type 14). Hydrogenolytic deb nzylation of 3-benzyl-1,7-dimethylxanthine (16), prepared by following this general synthetic route, furnished paraxanthine (26) in fair yield. Conversion of 26 into 3-(4-hydroxy-3-nitrobenzyl)-1,7-dimethylxanthine (24), isomeric with the bryozoan purine phidolopin (2), was effected through aralkylation with 4-(methoxymethoxy)-3-nitrobenzyl bromide (28) followed by O-deprotection. On the basis of proton nuclear magnetic resonance data for the 3,7-dialkylxanthines (3 and 9b-i) and 1,3,7-trialkylxanthines (5 and 14-22) thus prepared, reliable criteria for distinguishing signals of N-alkyl substituents at various positions are put forward.

A FACILE CONVERSION OF THE 1-METHYL GROUP TO THE 1-AMINO GROUP OF XANTHINE DERIVATIVES

A facile conversion of the 1-methyl group to the 1-amino group of caffeine and its analogues was carried out by the reaction with hydrazine hydrate: Refluxing of caffeine (Ia) with a large amount of hydrazine hydrate (30 eq. mole) without any other solvents gave 1-amino-3,7-dimethylxanthine (IIa) in 40percent yield.Similarly the reaction of 7-substituted 1,3-dimethylxanthines (Ib,Id-f) with hydrazine hydrate gave 7-substituted 1-amino-3-methylxanthines (IIb, IId-f) in 28-42percent yield.Deamination of these 7-substituted 1-amino-3-methylxanthines (IIa-b, IId-f) gave the corresponding theobromine derivatives (IVa-b, IVd-f) in 90-96percent yield.