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
• Article Data: 5

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

Chemical Properties

Pale Yellow Solid

Uses

Different sources of media describe the Uses of 1004-76-8 differently. You can refer to the following data:
1. 4,5-Diamino-6-hydroxy-2-mercaptopyrimidine exhibits antioxidative activity with potential for the treatment of oxidative stress-related diseases.
2. Key intermediate in the production of anticancer and analgesic agents.

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 
• 1672-48-6 4-amino-6-hydroxy-5-nitroso-2-thiopyrimidine 
• 1672-48-6 4-Amino-5-nitroso-6-oxo-1,2,3,6-tetrahydro-2-thiopyrimidine 
• 6232-21-9 2-amino-2-cyanoacetic acid 
• 17356-08-0 thiourea 

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 
• 51292-02-5 2,8-bis(methylthio)hypoxanthine 
• 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

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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.

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.