5440-00-6

Basic information

• Product Name: 5,6-DIAMINO-1,3-DIMETHYL URACIL
• Synonyms: 2,4(1H,3H)-Pyrimidinedione, 5,6-diamino-1,3-dimethyl-;3h)-pyrimidinedione,5,6-diamino-1,3-dimethyl-4(1h;5,6-Diamino-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione;Uracil, 5,6-diamino-1,3-dimethyl-;4,5-DIAMINO-1,3-DIMETHYLURACIL;5,6-DIAMINO-1,3-DIMETHYLPYRIMIDINE-2,4(1H,3H)-DIONE;5,6-DIAMINO-1,3-DIMETHYL URACIL;1,3-DIMETHYL-5,6-DIAMINOURACIL
• CAS NO: 5440-00-6
• Molecular Formula: C₆H₁₀N₄O₂
• Molecular Weight: 170.17
• EINECS: 226-621-9
• Product Categories: Nucleotides and Nucleosides;5-FOA;Bases & Related Reagents;Nucleotides;Building Blocks;C6 to C8;Chemical Synthesis;Heterocyclic Building Blocks;Pyrimidines
• Mol File: 5440-00-6.mol
• Article Data: 28

Chemical Properties

• Melting Point: 210-214 °C (dec.)(lit.)
• Boiling Point: 243.6±50.0℃ (760 Torr)
• Flash Point: 101.1±30.1℃
• Appearance: pale brown solid
• Density: 1.350±0.06 g/cm3 (20 ºC 760 Torr)
• Vapor Pressure: 0.0318mmHg at 25°C
• Refractive Index: 1.58
• Solubility: DMSO, Methanol
• PKA: 4.42±0.70(Predicted)
• BRN: 157451
• CAS DataBase Reference: 5,6-DIAMINO-1,3-DIMETHYL URACIL(CAS DataBase Reference)
• NIST Chemistry Reference: 5,6-DIAMINO-1,3-DIMETHYL URACIL(5440-00-6)
• EPA Substance Registry System: 5,6-DIAMINO-1,3-DIMETHYL URACIL(5440-00-6)

Safety Data

• WGK Germany: 3
• F: 10-34
• Hazardous Substances Data: 5440-00-6(Hazardous Substances Data)

Usage

Chemical Properties

Pale Brown Solid

Uses

Different sources of media describe the Uses of 5440-00-6 differently. You can refer to the following data:
1. 5,6-Diamino-1,3-dimethyluracil hydrate can be used as reactant involved in the synthesis of biologically active molecules including: 1H-Imidazol-1-yl substituted 8-phenylxanthines for use as adenosine receptor ligands ; Pyrimidinyl purinediones via cyclocondensation ; Theophylline derivatives as adenosine receptor antagonists ; Pteridine analogs for use as monoamine oxidase B and nitric oxide synthase inhibitors ; Fused tricyclic xanthines and Cadmium uraciliminoethylpyridine complexes for use as antiproliferatives against C6 glioma cells6.
2. 5,6-Diamino-1,3-dimethyl Uracil (cas# 5440-00-6) is a compound useful in organic synthesis.
3. Reactant involved in the synthesis of biologically active molecules including:1H-Imidazol-1-yl substituted 8-phenylxanthines for use as adenosine receptor ligandsPyrimidinyl purinediones via cyclocondensationTheophylline derivatives as adenosine receptor antagonistsPteridine analogs for use as monoamine oxidase B and nitric oxide synthase inhibitorsFused tricyclic xanthinesCadmium uraciliminoethylpyridine complexes for use as antiproliferatives against C6 glioma cells

Purification Methods

It recrystallises from EtOH. The hydrochloride has m 310o (from MeOH), and the perchlorate has m 246-248o. [UV: Bredereck et al. Chem Ber 92 583 1959, Taylor et al. J Am Chem Soc 77 2243 1955, Beilstein 25 III/IV 4133.]

InChI:InChI=1/C6H10N4O2/c1-9-4(8)3(7)5(11)10(2)6(9)12/h7-8H2,1-2H3

Upstream product

• 6632-68-4 6-amino-1,3-dimethyl-5-nitroso-1H-pyrimidine-2,4-dione 
• 58537-55-6 1,3-dimethyl-6-imino-5-isonitrosouracil 
• 43108-85-6 1,3-dimethyl-4-imino-5-isonitrosourazine 
• 10184-42-6 5-acetylamino-6-amino-1-methyl-1H-pyrimidine-2,4-dione 
• 1203-25-4 6-chloro-1,3-dimethyl-5-nitrouracil 
• 6642-31-5 6-Amino-1,3-dimethylbarbituric acid 
• 3346-61-0 6-amino-1,3-dimethyl-5-nitro-1H-pyrimidine-2,4-dione 
• 122707-25-9 6-amino-1,3-dimethyl-5-phenylazouracilate 
• 10184-41-5 5-acetylamino-6-amino-1,3-dimethyl-1H-pyrimidine-2,4-dione 
• 7597-60-6 1,3-dimethyl-4-amino-5-(formylamino)uracil 
• 39615-79-7 1-(2-cyanoacetyl)-1,3-dimethyl-urea 
• 6972-27-6 1,3-Dimethyl-6-chlorouracil 
• 769-42-6 1,3-dimethylbarbituric acid 
• 17743-04-3 1,3-dimethyl-6-iminouracil 

Downstream Products

• 58-55-9 theophylline 
• 109286-41-1 8-(4-chloro-benzyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 5770-30-9 8-Isobutyltheophyllin 
• 5429-31-2 8-(1-ethyl-propyl)-1,3-dimethyl-3,7-dihydro-purine-2,6-dione 
• 2879-15-4 8-benzyltheophylline 
• 2879-16-5 8-hydroxymethyltheophylline 
• 5429-48-1 1,3-dimethyl-8-[1]naphthylmethyl-3,7-dihydro-purine-2,6-dione 
• 91130-03-9 1.3-Dimethyl-2.4.6-trioxo-hexahydropteridin-carbonsaeure-(7)-methylamid 
• 5429-45-8 acetic acid-[4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-anilide] 
• 74039-62-6 8-allyltheophylline 
• 100144-13-6 N-(6-amino-1,3-dimethyl-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl)-lactamide 
• 964-45-4 1,3-dimethyl-7-phenyllumazine 
• 147699-92-1 1,3-dimethyl-8-(E)-styryl-3,7-dihydro-1H-purine-2,6-dione 
• 101092-80-2 4-(1,3-dimethyl-2,6-dioxo-2,3,6,7-tetrahydro-1H-purin-8-ylmethyl)-benzoic acid 

Relevant articles and documents

5,6-amino -1,3-dihydrocarbyl substituted uracil and preparation method thereof (by machine translation)

The invention belongs to the technical field of fine chemical engineering, and particularly relates to 5,6 -amino - 1111,dihydrocarbyl substituted uracil and a preparation method, of the dihydrocarbyl-substituted uracil 5,6 - diamino - 1111, 3-dihydrocarbyl- R substituted uracil, 5,6 - as shown in Formula (I). 1 And R2 Hydrochloride gas 1 - 10, each independently selected from hydrogen or carbon chain lengths of, carbon atoms according to the present invention 5,6 - of the present invention PVC diamino - 1111, 3-dihydrocarbyl-substituted uracil capable of absorbing, degradation processes, can also produce synergistic effect PVC by substituting labile chlorine atoms, with zinc stearate and calcium stearate PVC in combination with zinc stearate and calcium stearate for PVC to have better stabilization effect, The process performance, is improved PVC DEG, with good, stabilization effect PVC in combination. Heat stability 5,6 - can also be produced by the method, of the PVC present invention, for PVC, % of the stable effect of the present invention. (by machine translation)

Method for synthesizing caffeine

The invention discloses a method for synthesizing caffeine, and relates to the technical field of preparation of heterocyclic compounds containing purine ring systems. The preparation method comprisesthe following steps: mixing cyanoacetic acid and acetic anhydride at 30-80 DEG C for reaction, adding a solvent and dimethylurea, cooling to room temperature after reflux reaction is finished, filtering, concentrating filtrate, combining solids to obtain dimethylacetamide, adding liquid caustic soda to adjust the pH to 8-11, and reacting at 80-100 DEG C to generate dimethyl 4AU; the method comprises the following steps: completely dissolving dimethyl 4AU in formic acid, adding sodium nitrite, reacting at room temperature, adding a catalyst, keeping the temperature at 30-70 DEG C, recovering the catalyst after the reaction is finished, and concentrating mother liquor to recover formic acid, thereby obtaining dimethyl FAU; adding water and liquid caustic soda into dimethyl FAU, and carryingout a ring-closure reaction to obtain theophylline sodium salt; the theophylline sodium salt is subjected to methylation reaction and refining to obtain caffeine. The method has the advantages of accessible raw materials, mild and controllable reaction conditions, fewer steps, high yield and greatly higher product quality, is simple to operate, and can easily implement industrial production.

Synthesis and biological evaluation of novel xanthine derivatives as potential apoptotic antitumor agents

A series of novel xanthine/NO donor hybrids containing 1,3,8-trisubstituted or 1,8-disubstituted xanthine derivatives were designed and synthesized. The synthesized compounds were tested in a cell viability assay using human mammary gland epithelial cell line (MCF-10A) where all the compounds exhibited no cytotoxic effects and more than 90% cell viability at a concentration of 50 μM. The oxime containing compounds 7a-b and 17-24 were more active as antiproliferative agents than their non-oxime congeners 6a-b and 9-16. Hydroxyimino-phenethyl scaffold compounds 17-24 were more active than the hydroxyimino-ethyl phenyl acetamide 7a-b derivatives. Compounds 18–20 and 22-24 exhibited inhibition of EGFR with IC50 ranging from 0.32 to 2.88 μM. Compounds 18-20 and 22-24 increased the level of active caspase 3 by 4–8 folds, compared to the control cells in Panc-1 cell lines compared to doxorubicin as a reference drug. Compounds 18, 22 and 23 were the most caspase-3 inducers. Compounds 22 and 23 increased the levels of caspase-8 and 9 indicating activation of both intrinsic and extrinsic pathways and showed potent induction of Bax, down-regulation of Bcl-2 protein levels and over-expression of cytochrome c levels in Panc-1 human pancreas cancer cells. Compound 23 exhibited mainly cell cycle arrest at the Pre-G1 and G2/M phases in the cell cycle analysis of Panc-1 cell line. The drug likeness profiles of compounds 18-20 and 22-24 were predicted to have good to excellent drug likeness profiles specially compounds 18-20 and 23. Finally molecular docking study was performed at the EGFR active site to suggest thier possible binding mode. The hydroxyimino-phenethyl scaffold compounds 17-24 represent an interesting starting point to optimize their pharmacokinetics and pharmacodynamics profiles.