Production Method 1

851608-53-2

961-45-5

Reaction Conditions

1.1 Reagents: Sodium hydride Catalysts: Cuprous iodide Solvents: Tetrahydrofuran ;  5 min, reflux

Reference

Synthesis of Purines and Other Fused Imidazoles from Acyclic Amidines and Guanidines

Szczepankiewicz, Bruce G.; Rohde, Jeffrey J.; Kurukulasuriya, Ravi, Organic Letters, 2005, 7(9), 1833-1835

Production Method 2

964-04-5

961-45-5

Reaction Conditions

1.1 Reagents: Sodium hydroxide Solvents: Methanol ,  Water ;  3 h, reflux; cooled
1.2 Reagents: Acetic acid Solvents: Water ;  pH 5

Reference

Modulation of phosphoryl transferase activity of glutamine synthetase

, World Intellectual Property Organization, , ,

Production Method 3

60228-89-9

961-45-5

Reaction Conditions

1.1 Reagents: Triethyl orthoacetate Solvents: Dimethylformamide ;  10 h, reflux

Reference

Synthesis, DNA binding and antiviral activity of new uracil, xanthine, and pteridine derivatives

El-Sabbagh, Osama I.; El-Sadek, Mohamed E.; El-Kalyoubi, Samar; Ismail, Ibrahim, Archiv der Pharmazie (Weinheim, 2007, 340(1), 26-31

Production Method 4

6632-68-4

72037-57-1

961-45-5

Reaction Conditions

1.1 Solvents: Dimethylformamide

Reference

New purine synthesis

Yoneda, Fumio; Ogiwara, Kazuko; Kanahori, Michiko; Nishigaki, Sadao, Journal of the Chemical Society [Section] D: Chemical Communications, 1970, (17), 1068-9

Production Method 5

147623-02-7

961-45-5

Reaction Conditions

Reference

Reactions of 5,6-diamino-1,3-dimethyluracil with chalcone halo derivatives

Orlov, V. D.; Kolos, N. N.; Tueni, M.; Yur'eva, E. Yu.; Ivkov, S. M., Khimiya Geterotsiklicheskikh Soedinenii, 1992, (7), 947-54

Production Method 6

1670-14-0

7033-39-8

961-45-5

Reaction Conditions

1.1 Reagents: Oxygen Catalysts: Cupric acetate Solvents: 1,4-Dioxane ;  16 h, 100 °C

Reference

Influence of solvent and oxidant in copper-catalyzed synthesis of xanthine skeletons

Rahaman, Habibur, Asian Journal of Chemistry, 2022, 34(5), 1310-1312

Production Method 7

2067316-89-4

961-45-5

Reaction Conditions

1.1 Reagents: tert-Butyl peroxide Catalysts: Cuprous iodide Solvents: Dimethyl sulfoxide ;  4 h, rt → 90 °C

Reference

Concise Xanthine Synthesis through a Double-Amidination Reaction of a 6-Chlorouracil with Amidines using Base-Metal Catalysis

Morel, Benedicte; Franck, Philippe; Bidange, Johan; Sergeyev, Sergey; Smith, Dan A.; et al, ChemSusChem, 2017, 10(3), 624-628

Production Method 8

109507-50-8

961-45-5

Reaction Conditions

1.1 Solvents: Dimethylformamide

Reference

High chemical reactivity of 5-azidouracils and its synthetic application: novel synthesis of 8-substituted 1,3-dimethylxanthine derivatives

Hirota, Kosaku; Sako, Magoichi; Sajiki, Hironao, Heterocycles, 1997, 46, 547-554

Production Method 9

60228-89-9

961-45-5

Reaction Conditions

1.1 Reagents: Ammonia ,  Thionyl chloride Solvents: Water

Reference

Oxidative cyclization of 6-amino-5-benzylideneamino-1,3-dimethyluracils with thionyl chloride. A convenient synthesis of 8-substituted theophyllines

Senga, Keitaro; Shimizu, Kayoko; Nishigaki, Sadao, Chemical & Pharmaceutical Bulletin, 1977, 25(3), 495-7

Production Method 10

908822-55-9

961-45-5

Reaction Conditions

1.1 Reagents: Diisopropyl azodicarboxylate Solvents: 1,2-Dimethoxyethane ;  5 min, reflux; reflux; 25 min, reflux; reflux → rt

Reference

Synthesis of theophylline derivatives and study of their activity as antagonists at adenosine receptors

Hierrezuelo, Jesus; Manuel Lopez-Romero, J.; Rico, Rodrigo; Brea, Jose; Isabel Loza, M.; et al, Bioorganic & Medicinal Chemistry, 2010, 18(6), 2081-2088

Production Method 11

65-85-0

5440-00-6

961-45-5

Reaction Conditions

1.1 Solvents: Acetonitrile ,  Water ;  rt
1.2 Reagents: 2-Methylpropyl 2-(2-methylpropoxy)-1(2H)-quinolinecarboxylate (Merrifield resin-supported) ;  1 - 2 h, rt
1.3 Reagents: Sodium hydroxide Solvents: Acetonitrile ,  Water ;  rt → reflux; reflux; reflux → 0 °C
1.4 Reagents: Hydrochloric acid Solvents: Water ;  pH 5.0, 0 °C

Reference

Exploration of polystyrene-supported 2-isobutoxy-1-isobutoxycarbonyl-1,2-dihydroquinoline (PS-IIDQ) as new coupling agent for the synthesis of 8-substituted xanthine derivatives

Bandyopadhyay, Prabal; Sathe, Manisha; Sharma, Pratibha; Kaushik, M. P., Tetrahedron Letters, 2012, 53(35), 4631-4635

Production Method 12

1670-14-0

7033-39-8

961-45-5

Reaction Conditions

1.1 Reagents: Cesium carbonate Catalysts: N,N′-Dimethylethylenediamine ,  Copper bromide (CuBr2) Solvents: Toluene ;  36 h, 110 °C

Reference

Cu-Catalyzed C-H Activation Reaction: One-Pot Direct Synthesis of Xanthine and Uric Acid Derivatives from 5-Bromouracil

Hazra, Somjit; Mondal, Biplab; Roy, Brindaban; Rahaman, Habibur, Synlett, 2021, 32(17), 1757-1761

Production Method 13

54058-30-9

961-45-5

Reaction Conditions

1.1 Solvents: Nitrobenzene

Reference

Synthesis of purines by cyclization of the Michael-type adducts from 6-aminopyrimidines and 4-phenyl-1,2,4-triazoline-3,5-dione

Yoneda, Fumio; Kawamura, Mitsuko; Matsumoto, Shigeru; Higuchi, Masatsugu, Journal of the Chemical Society, 1977, (20), 2285-8

1,3-Dimethyl-8-phenylxanthine Raw materials

• Benzoic acid
• benzenecarboximidamide hydrochloride
• 5,6-diamino-1,3-dimethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione
• 1,3-Dimethyl-6,8-diphenyl-1H-pyrimido[4,5-b][1,4]diazepine-2,4(3H,9H)-dione
• N-(1,2,3,6-Tetrahydro-1,3-dimethyl-2,6-dioxo-4-pyrimidinyl)benzenecarboximidamide
• N-(5-Bromo-1,2,3,6-tetrahydro-1,3-dimethyl-2,6-dioxo-4-pyrimidinyl)benzenecarboximidamide
• 6-amino-5-(benzylideneamino)-1,3-dimethylpyrimidine-2,4-dione
• 4-Amino-1,3-dimethyl-5-nitrosouracil x-H2O
• 5-Bromo-1,3-dimethyluracil
• 2,4(1H,3H)-Pyrimidinedione, 5-bromo-1,3-dimethyl-6-[(phenylmethyl)amino]-
• Benzamide,N-(6-amino-1,2,3,4-tetrahydro-1,3-dimethyl-2,4-dioxo-5-pyrimidinyl)-
• 2,4(1H,3H)-Pyrimidinedione,6-amino-5-(3,5-dioxo-4-phenyl-1,2,4-triazolidin-1-yl)-1,3-dimethyl-
• 5-Amino-1,3-dimethyl-6-[(phenylmethylene)amino]-2,4(1H,3H)-pyrimidinedione
• Benzaldehyde, 2,2-dimethylhydrazone, (1E)-

1,3-Dimethyl-8-phenylxanthine Preparation Products

• 1,3-Dimethyl-8-phenylxanthine (961-45-5)

• 1. Enabling non-flammable Li-metal batteries via electrolyte functionalization and interface engineering?
  Jing Yu,Yu-Qi Lyu,Jiapeng Liu,Mohammed B. Effat,Junxiong Wu J. Mater. Chem. A, 2019,7, 17995-18002
• 2. Dissociation of large gaseous serine clusters produces abundant protonated serine octamer
  Jacob S. Jordan,Evan R. Williams Analyst, 2021,146, 2617-2625
• 3. Estimation of activation energy for electroporation and pore growth rate in liquid crystalline and gel phases of lipid bilayers using molecular dynamics simulations?
  Amit Kumar Majhi,Subbarao Kanchi,V. Venkataraman,K. G. Ayappa,Prabal K. Maiti Soft Matter, 2015,11, 8632-8640
• 4. Evolved polymerases facilitate selection of fully 2′-OMe-modified aptamers?
  Zhixia Liu,Tingjian Chen,Floyd E. Romesberg Chem. Sci., 2017,8, 8179-8182
• 5. Fe/Fe3C@C nanoparticles encapsulated in N-doped graphene–CNTs framework as an efficient bifunctional oxygen electrocatalyst for robust rechargeable Zn–air batteries?
  Zhiyan Chen,Nan Wu,Yaobing Wang,Bing Wang,Yingde Wang J. Mater. Chem. A, 2018,6, 516-526

Professional Introduction to 1,3-Dimethyl-8-phenylxanthine (CAS No. 961-45-5)

1,3-Dimethyl-8-phenylxanthine, a compound with the chemical formula C₁₃H₁₂N₄O₂, is a derivative of xanthine that has garnered significant attention in the field of pharmaceutical research due to its unique pharmacological properties. This compound, identified by its CAS number CAS No. 961-45-5, belongs to the xanthine class of alkaloids, which are well-known for their stimulant effects on the central nervous system. The structural modification of xanthine by introducing dimethyl and phenyl groups at specific positions enhances its biological activity, making it a subject of extensive study in drug development.

The pharmacological profile of 1,3-Dimethyl-8-phenylxanthine is characterized by its ability to interact with multiple adenosine receptors, which are crucial for regulating various physiological processes such as sleep, cognition, and cardiovascular function. Adenosine receptors are classified into four subtypes (A1, A2A, A2B, and A3), and 1,3-Dimethyl-8-phenylxanthine exhibits selective binding affinity for these receptors. This selectivity is a key factor in determining its therapeutic potential and side effect profile.

Recent studies have highlighted the potential of 1,3-Dimethyl-8-phenylxanthine as a therapeutic agent in conditions associated with adenosine receptor dysfunction. For instance, research has demonstrated its efficacy in improving cognitive function in animal models of Alzheimer's disease by modulating A2A receptor activity. The compound's ability to enhance synaptic plasticity and neuroprotection makes it an attractive candidate for further clinical investigation.

In addition to its cognitive effects, 1,3-Dimethyl-8-phenylxanthine has shown promise in the treatment of cardiovascular disorders. Studies indicate that this compound can exert vasodilatory effects by inhibiting phosphodiesterase enzymes, which play a role in regulating blood pressure and vascular tone. The phenyl group in its structure contributes to its interaction with these enzymes, thereby modulating cardiovascular function.

The synthesis of 1,3-Dimethyl-8-phenylxanthine involves multi-step organic reactions that require precise control over reaction conditions to ensure high yield and purity. The dimethylation and phenylation steps are critical in achieving the desired structural modifications. Advanced synthetic methodologies, including catalytic hydrogenation and palladium-catalyzed cross-coupling reactions, have been employed to optimize the synthesis process. These techniques not only improve efficiency but also minimize byproduct formation.

The analytical characterization of 1,3-Dimethyl-8-phenylxanthine is essential for ensuring its quality and consistency. High-performance liquid chromatography (HPLC), nuclear magnetic resonance (NMR) spectroscopy, and mass spectrometry (MS) are commonly used analytical techniques for confirming the identity and purity of the compound. These methods provide detailed structural information and help in identifying any impurities that may affect its pharmacological activity.

The pharmacokinetic properties of 1,3-Dimethyl-8-phenylxanthine have been studied to understand its absorption, distribution, metabolism, and excretion (ADME) profiles. Preclinical studies have shown that this compound exhibits moderate oral bioavailability and a relatively long half-life, suggesting potential for once-daily dosing in therapeutic applications. Further research is ongoing to optimize dosage regimens and minimize any potential adverse effects.

In conclusion, 1,3-Dimethyl-8-phenylxanthine (CAS No. 961-45-5) is a promising pharmacological agent with diverse therapeutic applications. Its selective interaction with adenosine receptors makes it valuable in treating neurological and cardiovascular disorders. The compound's synthesis involves sophisticated organic chemistry techniques, while its analytical characterization ensures high purity and consistency. Ongoing research continues to explore its full therapeutic potential and optimize its pharmacokinetic properties for clinical use.

• 75922-48-4(1,3-Diethyl-8-phenylxanthine)
• 57000-13-2(1H-Purine-2,6-dione,3,9-dihydro-1,3-dimethyl-8-[(phenylmethyl)amino]-)
• 19844-93-0(3-benzyl-2,3,6,7-tetrahydro-1H-purine-2,6-dione)
• 2098070-20-1(2-(3-(Pyridin-3-yl)-1H-pyrazol-1-yl)acetimidamide)
• 2680771-01-9(4-cyclopentyl-3-{(prop-2-en-1-yloxy)carbonylamino}butanoic acid)
• 1444113-98-7(N-(3-cyanothiolan-3-yl)-2-[(2,2,2-trifluoroethyl)sulfanyl]pyridine-4-carboxamide)
• 332062-08-5(Fmoc-S-3-amino-4,4-diphenyl-butyric acid)
• 1270529-38-8(1,2,3,4,5,6-Hexahydro-[2,3]bipyridinyl-6-ol)
• 941977-17-9(N'-(3-chloro-2-methylphenyl)-N-2-(dimethylamino)-2-(naphthalen-1-yl)ethylethanediamide)
• 2138166-62-6(2,2-Difluoro-3-[methyl(2-methylbutyl)amino]propanoic acid)