1005-39-6

Basic information

• Product Name: 4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE
• Synonyms: 2-(Methylsulfanyl)-4,6-pyrimidinediamine;2-Methylthio-4,6-diaminopyrimidine;Pyrimidine, 4,6-diamino-2-(methylthio)-;4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE;AKOS USSH-4110074;AKOS BBS-00007356;6-AMINO-2-(METHYLTHIO)-4-PYRIMIDINYLAMINE;2-methylthiopyrimidine-4,6-diamine
• CAS NO: 1005-39-6
• Molecular Formula: C₅H₈N₄S
• Molecular Weight: 156.21
• EINECS: 213-735-9
• Mol File: 1005-39-6.mol
• Article Data: 3

Chemical Properties

• Melting Point: 189-193 °C
• Boiling Point: 413.5 °C at 760 mmHg
• Flash Point: 203.9 °C
• Appearance: light yellow crystalline powder
• Density: 1.38 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.671
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• PKA: 5.15±0.10(Predicted)
• BRN: 127235
• CAS DataBase Reference: 4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE(1005-39-6)
• EPA Substance Registry System: 4,6-DIAMINO-2-METHYLMERCAPTOPYRIMIDINE(1005-39-6)

Safety Data

• Hazard Codes: Xn
• Statements: 36/37/38-22
• Safety Statements: 36/37/39-26
• RIDADR: 2811
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 1005-39-6(Hazardous Substances Data)

Usage

Chemical Properties

light yellow crystalline powder

Uses

4,6-Diamino-2-(methylthio)pyrimidine can reacts with 3-Ethoxy-acrylic acid ethyl ester to get 4-Amino-2-methylsulfanyl-8H-pyrido[2,3-d]pyrimidin-7-one.

InChI:InChI=1/C5H8N4S/c1-10-5-8-3(6)2-4(7)9-5/h2H,1H3,(H4,6,7,8,9)

Upstream product

• 1004-39-3 4,6-diaminopyrimidine-2(1H)-thione 
• 74-88-4 methyl iodide 
• 1004-39-3 4,6-diamino-2-mercaptopyrimidine 
• 1005-38-5 4-amino-6-chloro-2-methylthiopyrimidine 

Downstream Products

• 102712-39-0 4-(4,6-Diamino-2-methylsulfanyl-pyrimidin-5-ylazo)-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide 
• 121087-93-2 1-(6-amino-2-methylthiopyrimidin-4-yl)-3-(4-chlorophenyl)thiourea 
• 6979-72-2 2-methylsulfanyl-5-phenylazo-pyrimidine-4,6-diamine 
• 121087-83-0 1-(6-amino-2-methylthiopyrimidin-4-yl)-3-benzoylthiourea 
• 121087-91-0 1-(6-amino-2-methylthiopyrimidin-4-yl)-3-benzylurea 
• 36707-42-3 diethyl 2-((6-amino-2-(methylthio)pyrimidin-4-ylamino)methylene)malonate 
• 1309571-71-8 4-amino-5-(3,5-dibromophenyl)-2-(methylsulfanyl)-5,9-dihydrofuro[3',4':5,6]pyrido [2,3-d]pyrimidin-6(8H)-one 
• 1309571-70-7 4-amino-2-(methylsulfanyl)-5-(3,4,5-trimethoxyphenyl)-5,9-dihydrofuro[3',4':5,6]pyrido[2,3-d]pyrimidin-6(8H)-one 
• 36707-43-4 [(6-acetylamino-2-methylsulfanyl-pyrimidin-4-ylamino)-methylene]-malonic acid diethyl ester 
• 36707-44-5 4-acetylamino-2-methylsulfanyl-5-oxo-5,8-dihydro-pyrido[2,3-d]pyrimidine-6-carboxylic acid ethyl ester 
• 1431-40-9 2-methylsulfanyl-pyrimidine-4,5,6-triamine 
• 1198-83-0 2-(methylthio)-7H-purin-6-amine 
• 102712-28-7 4-(7-Amino-5-methylsulfanyl-[1,2,3]triazolo[4,5-d]pyrimidin-2-yl)-N-(5-methyl-isoxazol-3-yl)-benzenesulfonamide 
• 102712-34-5 5-Methylsulfanyl-2-phenyl-2H-[1,2,3]triazolo[4,5-d]pyrimidin-7-ylamine 

Relevant articles and documents

Imidazopyridine- and purine-thioacetamide derivatives: Potent inhibitors of nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1)

Nucleotide pyrophosphatase/phosphodiesterase 1 (NPP1) belongs to the family of ecto-nucleotidases, which control extracellular nucleotide, nucleoside, and (di)phosphate levels. To study the (patho)physiological roles of NPP1 potent and selective inhibitors with drug-like properties are required. Therefore, a compound library was screened for NPP1 inhibitors using a colorimetric assay with p-nitrophenyl 5′-thymidine monophosphate (p-Nph-5′-TMP) as an artificial substrate. This led to the discovery of 2-(3H-imidazo[4,5-b]pyridin-2-ylthio)-N-(3,4-dimethoxyphenyl)acetamide (5a) as a hit compound with a Ki value of 217 nM. Subsequent structure-activity relationship studies led to the development of purine and imidazo[4,5-b]pyridine analogues with high inhibitory potency (Ki values of 5.00 nM and 29.6 nM, respectively) when assayed with p-Nph-5′-TMP as a substrate. Surprisingly, the compounds were significantly less potent when tested versus ATP as a substrate, with Ki values in the low micromolar range. A prototypic inhibitor was investigated for its mechanism of inhibition and found to be competitive versus both substrates.

Docking studies and development of novel 5-heteroarylamino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines as potential antimalarials

MOE-Dock (Docking software) was used to predict the binding modes of 10 novel and potent 5-substituted amino-2,4-diamino-8-chloropyrimido-[4,5-b]quinolines (compounds I-X) as part of our antimalarial drug development programme. This was done by analyzing the interaction of these compounds with the active sites of 11 enzymes present in Plasmodium falciparum and based on this, effective binding was observed to enzyme P. falciparum glutathione reductase (PfGR). The binding scores for compounds I-X with PfGR were also congruent with their antimalarial activity. Three additional analogs were then designed and synthesized based on the above docking study and the pharmacophoric requirements for this class.