636-26-0

Basic information

• Product Name: 4-Hydroxy-5-methyl-2-mercaptopyrimidine
• Synonyms: 2,3-dihydro-5-methyl-2-thioxo-4(1h)-pyrimidinone;2-thio-thymin;2-Thiothymine;5-Methyl-2-thioxo-2,3-dihydro-4(1H)-pyrimidinone;Thiothymine;Thymine, 2-thio-;Uracil, 5-methyl-2-thio-;5-METHYL-2-THIOURACIL
• CAS NO: 636-26-0
• Molecular Formula: C₅H₆N₂OS
• Molecular Weight: 142.18
• Product Categories: PYRIMIDINE;Pyridines, Pyrimidines, Purines and Pteredines
• Mol File: 636-26-0.mol

Chemical Properties

• Melting Point: 283-286°C
• Boiling Point: 329.7oC at 760 mmHg
• Flash Point: 153.2oC
• Appearance: white crystalline powder
• Density: 1.36
• Vapor Pressure: 9.11E-05mmHg at 25°C
• Refractive Index: 1.6430 (estimate)
• Storage Temp.: Sealed in dry,Room Temperature
• PKA: pKa 7.71 (Uncertain)
• Water Solubility: 509mg/L(25 oC)
• Stability: Stable but may be heat or light sensitive. Incompatible with strong oxidizing agents.
• BRN: 120488
• CAS DataBase Reference: 4-Hydroxy-5-methyl-2-mercaptopyrimidine(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxy-5-methyl-2-mercaptopyrimidine(636-26-0)
• EPA Substance Registry System: 4-Hydroxy-5-methyl-2-mercaptopyrimidine(636-26-0)

Safety Data

• Hazard Codes: Xi
• Statements: 22-40-36/37/38
• Safety Statements: 22-36/37-26
• RTECS: XP2108500
• Hazardous Substances Data: 636-26-0(Hazardous Substances Data)

Usage

Chemical Properties

white crystalline powder

General Description

White crystalline solid.

Air & Water Reactions

Insoluble in water.

Reactivity Profile

4-Hydroxy-5-methyl-2-mercaptopyrimidine is heat sensitive and may be light sensitive.

Fire Hazard

Flash point data for 4-Hydroxy-5-methyl-2-mercaptopyrimidine are not available. 4-Hydroxy-5-methyl-2-mercaptopyrimidine is probably combustible.

InChI:InChI=1/C5H6N2OS/c1-3-2-6-5(9)7-4(3)8/h2H,1H3,(H2,6,7,8,9)

Upstream product

• 36056-90-3 ethyl 3,3-diethoxy-2-methylpropionate 
• 17356-08-0 thiourea 
• 54843-13-9 α-formyl propionate d'ethyle 
• 4401-71-2 1,3-dimethylthymine 

Downstream Products

• 103860-39-5 α-(5-methyl-6-oxo-1,6-dihydro-pyrimidin-2-ylmercapto)-isobutyric acid 
• 20651-30-3 2-methylthio-3,4-dihydro-5-methylpyrimidin-4-one 
• 17758-52-0 5-methyl-4(3H)-pyrimidinone 
• 6217-61-4 5-methylthio-2-thiouracil 
• 33575-17-6 3,4-dihydro-2-hydrazino-5-methylpyrimidin-4-one 
• 78932-24-8 5-Methyl-2-(4-nitro-benzylsulfanyl)-3H-pyrimidin-4-one 
• 78932-22-6 2-benzylmercapto-5-methyl-3H-pyrimidin-4-one 
• 117999-08-3 1-(2-Benzyloxy-1-benzyloxymethyl-ethoxymethyl)-5-methyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 65-71-4 thymin 
• 180145-58-8 2-<(E)-cinnamylthio>-5-methyl-4(3H)-pyrimidinone 
• 65-71-4 2,4-dihydroxy-5-methylpyrimidine 
• 299464-94-1 3-amino-6-methyl-5-oxothiazolo[3,2-a]pyrimidine-2-carbonitrile 
• 13480-95-0 2-ethylthio-3,4-dihydro-5-methylpyrimidin-4-one 
• 832146-82-4 5-methyl-2-phenyl-8-thia-2,3b,7-triaza-cyclopenta[a]indene-1,3,4-trione 

Relevant articles and documents

Synthesis and biological evaluation of DAPY-DPEs hybrids as non-nucleoside inhibitors of HIV-1 reverse transcriptase

A series of new DAPY-DPEs hybrids, combined the important pharmacophores of DAPYs and DPEs, has been synthesized and biologically evaluated for their anti-HIV activities against wild-type HIV-1 strain IIIB, double RT mutant (K103N + Y181C) strain RES056 and HIV-2 strain ROD in MT-4 cell cultures. Many promising candidates with potent inhibitory activity (wild-type) within the EC50 range from 0.16 to 0.013 μM were obtained. In particular, 3c, 3p, 3r and 3s displayed low nM level EC50 values (35, 13, 50 and 17 nM, respectively) and high selectivity (9342, 25131, 2890 and 11338, respectively), which were much more potent than NVP (EC50 = 0.31 μM, SI = 48), 3TC (EC50 = 2.24 μM, SI > 39), DDI (EC50 = 23.20 μM, SI > 9) and DLV (EC50 = 0.65 μM, SI > 67), and comparable to AZT (EC50 = 0.0071 μM, SI > 13144) and EFV (EC50 = 0.0062 μM, SI > 1014). The HIV-1 reverse transcriptase inhibitory assay confirmed that these DAPY-DPEs hybrids targeted HIV-1 RT. Molecular simulation was performed to investigate the potential binding mode of the newly synthesized compounds. And reasonable explanation for the activity results was discussed with docking method.

Design, synthesis and biological evaluation of cycloalkyl arylpyrimidines (CAPYs) as HIV-1 NNRTIs

A series of 18 cycloalkyl arylpyrimidines (CAPYs) were designed from lead compounds diarylpyrimidines (DAPYs), synthesized and evaluated for in vitro anti-HIV activity. Among them, the compound 1p displayed potent anti-HIV-1 activity against WT HIV-1 with an EC50 value of 0.055 μM and a selectivity index (SI) >7290. The preliminary structure-activity relationship (SAR) of this new series of compounds was also investigated, which enriched the SAR of diarylpyrimidines (DAPYs).