8-Bromo-3-methyl-1H-purine-2,6(3H,7H)-dione

Base Information

• Chemical Name: 8-Bromo-3-methyl-1H-purine-2,6(3H,7H)-dione
• CAS No.: 93703-24-3
• Molecular Formula: C6H5BrN4O2
• Molecular Weight: 245.035
• Hs Code.: 29339900
• European Community (EC) Number: 819-117-0
• DSSTox Substance ID: DTXSID50364285
• Nikkaji Number: J3.359.719C
• Wikidata: Q72447051
• Mol file: 93703-24-3.mol

Synonyms:93703-24-3;8-Bromo-3-methyl-1H-purine-2,6(3H,7H)-dione;8-BROMO-3-METHYL-XANTHINE;8-bromo-3-methylxanthine;8-bromo-3-methyl-7H-purine-2,6-dione;3-methyl-8-bromoxanthine;8-Bromo-3-methyl-3,7-dihydropurine-2,6-dione;8-bromo-3-methyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione;8-BROMO-3-METHYL-3,7-DIHYDRO-PURINE-2,6-DIONE;8-bromo-3-methyl-3,7-dihydro-1H-purine-2,6-dione;MFCD00462528;1H-Purine-2,6-dione, 8-bromo-3,7-dihydro-3-methyl-;8-BROMO-3,9-DIHYDRO-3-METHYL-1H-PURINE-2,6-DIONE;C6H5BrN4O2;8-bromo3-Methyl-xanthine;3-methyl-8-bromo-xanthine;8-bromo-3-methyl xanthine;8-Bromo-3-methyl-3,9-dihydro-purine-2,6-dione;Oprea1_287813;Oprea1_865455;AMY492;SCHEMBL1241218;SCHEMBL15924314;DTXSID50364285;HMS1649I20;BCP12331;BBL012668;STK656575;STK803300;AKOS000267178;AKOS005587316;CS-O-32157;CS-W019625;AC-26251;AS-19142;SY038324;B4134;FT-0688013;EN300-134139;MLS-0463078.0001;8-bromo-3-methyl-1H-purine-2,6(3H,9H)-dione;A855277;SR-01000506601;8-bromo-3-methyl-1H-purine-2,6(3H,7H)- dione;J-519386;SR-01000506601-1;F0373-0001;F0381-3715;8-bromo-6-hydroxy-3-methyl-3,7-dihydro-2H-purin-2-one;8-bromo-3-methyl-1H-purine-2,6(3H,7H)-dione;8-Bromo-3-methylxanthine

Chemical Property of 8-Bromo-3-methyl-1H-purine-2,6(3H,7H)-dione

Chemical Property:

• Melting Point: 300°C(lit.)
• PKA: 7.65±0.20(Predicted)
• PSA: 83.54000
• Density: 1.975 g/cm³
• LogP: -0.28760
• Storage Temp.: under inert gas (nitrogen or Argon) at 2–8 °C
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 0
• Exact Mass: 243.95959
• Heavy Atom Count: 13
• Complexity: 271

Purity/Quality:

99.5%min ^*data from raw suppliers

8-Bromo-3,9-dihydro-3-methyl-1H-purine-2,6-dione ^*data from reagent suppliers

Safty Information:

• Statements: 22
• Safety Statements: 26-36/37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CN1C2=C(C(=O)NC1=O)NC(=N2)Br
• Uses: 8-Bromo-3,9-dihydro-3-methyl-1H-purine-2,6-dione, is a substituted derivative of Xanthine (X499950), found in animal organs, yeast, potatoes, coffee beans, tea. It can also be used for the synthesis of Linagliptin (L465900), which is a novel potent and selective dipeptidyl peptidase-4 (DPP-4) inhibitor with potential use in the treatment of type 2 diabetes.

Technology Process of 8-Bromo-3-methyl-1H-purine-2,6(3H,7H)-dione

There total 8 articles about 8-Bromo-3-methyl-1H-purine-2,6(3H,7H)-dione which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 97.0%

C6H7BrN4O2 → 3-methyl-8-bromoxanthine (93703-24-3)

Guidance literature:

With N-Bromosuccinimide; potassium carbonate; In 1,2-dichloro-ethane; at 60 ℃; for 5h; Reagent/catalyst; Solvent; Temperature;

Reference yield: 96.6%

3-methylxanthine (1076-22-8) → 3-methyl-8-bromoxanthine (93703-24-3)

Guidance literature:

With bromine; sodium acetate; In acetic acid; at 50 - 65 ℃; for 3h;

Reference yield: 84.0%

formic acid (64-18-6) + 5,6-diamino-1-methyluracil (6972-82-3) → 3-methyl-8-bromoxanthine (93703-24-3)

Guidance literature:

formic acid; 5,6-diamino-1-methyluracil; In water; for 2h; Reflux;

With sodium hydroxide; In water; at 100 ℃; for 16h;

With bromine; sodium acetate; acetic acid; at 66 ℃; for 3h;

upstream raw materials:

3-methyl-8-nitroxanthine

3-methylxanthine

formic acid

5,6-diamino-1-methyluracil

Downstream raw materials:

8-bromo-7-(but2-yn-1-yl)-3-methyl-3,7-dihydro-1H-purine-2,6–dione

1,3-dimethyl-6-phenylthiazolo[2,3-f]purine-2,4(1H,3H)-dione

1-Methyl-6-phenyl-1H-thiazolo[2,3-f]purine-2,4-dione

6-(4-Chloro-phenyl)-1-methyl-1H-thiazolo[2,3-f]purine-2,4-dione

Refernces

• 1、 Konduri, Srihari,Prashanth, Jyothi,Krishna, Vagolu Siva,Sriram, Dharmarajan,Behera,Siegel, Dionicio,Rao, Koya Prabhakara. "Design and synthesis of purine connected piperazine derivatives as novel inhibitors of Mycobacterium tuberculosis". supporting information. . Retrieved 2020/09/16.
• 2、 Battula, Kumara Swamy,Nagavelli, Vasudeva Reddy,Narsimha, Sirassu,Ravinder, M.,Reddy, Y. N.. "Design, synthesis and biological evaluation of novel 1,2,3-triazole-based xanthine derivatives as DPP-4 inhibitors". . . Retrieved 2020/04/07.