1004-76-8

Basic information

• Product Name: 2-Mercapto-4-hydroxy-5,6-diaminopyrimidine
• Synonyms: 4,5-DIAMINO-6-HYDROXY-2-PYRIMIDINETHIOL HEMISULFATE- 1,5-HYDRATE 97%;5,6-Diamino-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one;4(1H)-Pyrimidinone, 5,6-diamino-2,3-dihydro-2-thioxo-;4,5-Diamino-6-hydroxy-2-mercaptopyrimidine, tech. 90%;2-Mercapto-5,6-diaminopyrimidine-4(3H)-one;2-Mercapto-5,6-diaminopyrimidine-4-ol;5,6-Diamino-2,3-dihydro-2-thioxopyrimidin-4(1H)-one;-13C,15N 2-Mercapto-4,5-diaMino-6-hydroxypyriMidine-13C,15N
• CAS NO: 1004-76-8
• Molecular Formula: C₄H₆N₄OS
• Molecular Weight: 158.18
• EINECS: 213-727-5
• Product Categories: Amines;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds;Building Blocks;C4 to C5;Chemical Synthesis;Heterocyclic Building Blocks;Pyrimidines;Pyrimidine series;APIs & Intermediate;Pyrimidine;Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 1004-76-8.mol

Chemical Properties

• Melting Point: >300 °C(lit.)
• Boiling Point: 473 °C at 760 mmHg
• Flash Point: 239.9 °C
• Appearance: /
• Density: 1.66 g/cm³
• Vapor Pressure: 1.43E-09mmHg at 25°C
• Refractive Index: 1.776
• Storage Temp.: 2-8°C
• PKA: 8.10±0.60(Predicted)
• CAS DataBase Reference: 2-Mercapto-4-hydroxy-5,6-diaminopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 2-Mercapto-4-hydroxy-5,6-diaminopyrimidine(1004-76-8)
• EPA Substance Registry System: 2-Mercapto-4-hydroxy-5,6-diaminopyrimidine(1004-76-8)

Safety Data

• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-36
• WGK Germany: 3
• Hazardous Substances Data: 1004-76-8(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2-Mercapto-4-hydroxy-5,6-diaminopyrimidine is used as a key intermediate for the production of anticancer and analgesic agents. Its role in the synthesis of these medications is crucial, as it contributes to the development of drugs that can help combat cancer and alleviate pain.
Used in Antioxidant Applications:
In the field of antioxidant research and development, 2-Mercapto-4-hydroxy-5,6-diaminopyrimidine is used for its antioxidative activity. This property makes it a potential therapeutic agent for the treatment of oxidative stress-related diseases, which can have a significant impact on human health.
Used in Oxidative Stress-Related Disease Treatment:
2-Mercapto-4-hydroxy-5,6-diaminopyrimidine is also used as a therapeutic agent for the treatment of diseases associated with oxidative stress. Its antioxidative properties allow it to potentially mitigate the harmful effects of oxidative stress on the body, offering a promising avenue for medical research and treatment development.

InChI:InChI=1/C4H6N4OS/c5-1-2(6)7-4(10)8-3(1)9/h5H2,(H4,6,7,8,9,10)

Upstream product

• 1004-40-6 6-Amino-2-thiouracil 
• 57573-52-1 4-methylbenzene diazonium 
• 6232-21-9 2-amino-2-cyanoacetic acid 
• 17356-08-0 thiourea 
• 1672-48-6 4-Amino-5-nitroso-6-oxo-1,2,3,6-tetrahydro-2-thiopyrimidine 
• 1672-48-6 4-amino-6-hydroxy-5-nitroso-2-thiopyrimidine 

Downstream Products

• 91184-09-7 8-methyl-2-thioxo-1,2,3,7-tetrahydro-purin-6-one 
• 2487-40-3 2-thioxanthine 
• 94088-97-8 6-methyl-2-thioxo-2,3-dihydro-1H,8H-pteridine-4,7-dione 
• 6967-57-3 7-methyl-2-thioxo-1,2,3,5-tetrahydro-pteridine-4,6-dione 
• 6306-85-0 7-Oxo-5-thioxo-<1.2.5>thiadiazolo<3,4-d>pyrimidin-(4H,6H) 
• 54030-51-2 6,7-dimethyl-2-thioxo-2,3-dihydropteridin-4(1H)-one 
• 14892-97-8 6,7-diphenyl-1,2-dihydro-2-thioxopteridin-4(3H)-one 
• 15986-31-9 2-thio-6,8-dioxopurine 
• 1468-26-4 8-azaxanthine 
• 31571-52-5 5-thioxo-1,4,5,6-tetrahydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one 
• 1672-50-0 5,6-diamino-4(3H)-pyrimidinone 
• 1356834-65-5 5,6-diamino-2-(4-tert-butylbenzylthio)pyrimidin-4(3H)-one 
• 64194-62-3 4-amino-5-formamido-6-hydroxy-2-mercaptopyrimidine 
• 14091-63-5 2-Mercapto-8-phenyl-1,9-dihydro-purin-6-one 

Relevant articles and documents

Discovery and evaluation of new compounds targeting ribosomal protein S1 in antibiotic-resistant Mycobacterium Tuberculosis

The emergence of antibiotic-resistant Mycobacterium Tuberculosis (Mtb) infections compels new treatment strategies, of which targeting trans-translation is promising. During the trans-translation process, the ribosomal protein S1 (RpsA) plays a key role, and the Ala438 mutant is related to pyrazinamide (PZA) resistance, which shows its effects after being hydrolysed to pyrazinoic acid (POA). In this study, based on the structure of the RpsA C-terminal domain (RpsA-CTD) and POA complex, new compounds were designed. After being synthesized, the compounds were tested in vitro with saturation transfer difference (STD), fluorescence quenching titration (FQT) and chemical shift perturbation (CSP) experiments. Finally, six of the 17 new compounds have high affinity for both RpsA-CTD and its Ala438 deletion mutant. The active compounds provide new choices for targeting trans-translation in Mtb, and the analysis of the structure-activity relationships will be helpful for further structural modifications based on derivatives of 2-((hypoxanthine-2-yl)thio)acetic acid and 2-((5-hydroxylflavone-7-yl)oxy)acetamide.

Synthesis, experimental and computational studies of N-(4-amino-6-oxo-1,6-dihydropyrimidin-5-yl)benzamide

Background: Blockade of kainate receptors is an emerging strategy to treat neurodegenera-tive diseases, including Parkinson’s disease as well as to treat epilepsy. In particular, non-competitive antagonists of kainate receptors are promising due to the expected good safety profile. We present here synthesis, experimental and computational studies of N-(4-amino-6-oxo-1,6-dihydropyrimidin-5-yl)benzamide which is an intermediate in the synthesis of hypoxanthine derivatives which were designed as non-competitive antagonists of kainate GluK1/GluK2 receptors. Method: The title compound was obtained in a five-step synthesis protocol and characterized used X-ray crystallography and experimental and computed spectra. Results: The presented detailed X-ray studies of the title compound confirm the reaction course. The title compound crystallizes in triclinic P-1 space group. The asymmetric unit comprises two independent molecules of the compound (A and B) and a DMF solvent molecule. The interpretation of IR spectra was facilitated by Potential Energy Distribution (PED) analysis. The low value of HOMO-LUMO gap indicates that the studied compound is relatively reactive. Conclusion: The title compound is a well-characterized intermediate which will be subjected to cycli-zation to hypoxanthine derivative designed as non-competitive antagonist of kainate GluK1 and GluK2 receptors.

N-Alkylation of 2,6-dichloropurine hydrochloride with a variety of alcohols over alumina catalyst

2,6-Dichloropurine hydrochloride reacts with various types of alcohols using different alumina catalysts and converts into its N-9-alkyl-2-chloro-6- hydroxy-9H-purine products to an extent of 49-74%. The product selectivity depends on the stability of carbocation generated from the alcohol. More stable carbocation formulates both N-7 and N-9-alkyl-2,6-dichloropurine products, whereas the less stable carbocation results in exclusively N-9-alkyl-2-chloro-6- hydroxy-9H-purine. The catalytic activity of alumina prepared using the sol-gel method has larger Brunauer, Emmett, and Teller (BET) surface area and hence shows significantly greater catalytic activity than the commercially available alumina samples. Copyright

New N6-substituted 8-alkyl-2-phenylmethylsulfanyl-adenines. II [1]

Title compounds bearing substituents on C(2), C(6) and C(8) were prepared from a newly synthesized pyrimidine derivative 11. The new pyrimidine 11 was generated from compound 2 through two different synthetic schemes. In one pathway, compound 2 was nitrosated, reduced and alkylated to produce compounds 9, 10 and 11 respectively (Scheme). In an alternate route using compound 2 as the starting material, a coupling reaction using the diazonium salt derived from p-methylaniline afforded the azo derivative 7, which was subsequently alkylated and reductively cleaved to form compounds 8 and 11 respectively (See Scheme). Compound 11 was annulated to the corresponding hypoxanthine derivatives 12-14; compounds 12 and 13 were chlorinated with phosphorus oxychloride, then reacted with amines to yield compound 17 and 20 respectively. Compounds 21, 22 and 23 were obtained by oxidation of the corresponding sulfide as depicted in Scheme. Alkylation of the thiol function of 1 gave a mixture of 3 and 4. Compound 3 was chlorinated to 5. Nitration of 5 resulted in electrophilic aromatic substitution of the aryl ring and concomitant oxidation of the sulfide to the sulfoxide, producing 6.

A prototype solid phase synthesis of pteridines and related heterocyclic compounds

The development of a versatile solid phase synthesis of bicyclic polyaza heterocycles including pteridines, purines, and deazapurines is described. The strategy comprises the linking of a pre-formed pyrimidine through a thioether at the 2 or 4 position to a polystyrene resin, the cyclisation of the second ring, and the direct or oxidative cleavage of the product from the resin by nucleophilic substitution. This provides not only for substituent variation in the second ring, but also for variation at the site of cleavage. Limitations in the scope of the methodology are set by the intrinsic reactivity of pyrimidinyl 2- or 4-thioethers which, whilst undergoing ready nitration at C5, are surprisingly difficult to alkylate and acylate.