136160-18-4

Basic information

• Product Name: 5-methyl-6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione
• Synonyms: 2,4-pyrimidinediol, 5-methyl-6-(phenylthio)-; 5-methyl-6-(phenylsulfanyl)pyrimidine-2,4-diol; 6-(Phenylthio)thymine
• CAS NO: 136160-18-4
• Molecular Formula: C₁₁H₁₀N₂O₂S
• Molecular Weight: 234.2743
• Mol File: 136160-18-4.mol

Chemical Properties

• Density: 1.37g/cm³
• Refractive Index: 1.66
• CAS DataBase Reference: 5-methyl-6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione(CAS DataBase Reference)
• NIST Chemistry Reference: 5-methyl-6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione(136160-18-4)
• EPA Substance Registry System: 5-methyl-6-(phenylsulfanyl)pyrimidine-2,4(1H,3H)-dione(136160-18-4)

Safety Data

• Hazardous Substances Data: 136160-18-4(Hazardous Substances Data)

Upstream product

• 31458-38-5 6-iodo-5-methylpyrimidine-2,4(1H,3H)-dione 
• 136160-46-8 N₁-(methoxymethyl)thymine 
• 65-71-4 thymin 
• 136160-17-3 1-(methoxymethyl)-6-phenylthiothymine 
• 1627-28-7 6-chloro-5-methylpyrimidine-2,4(1H,3H)-dione 
• 2417-22-3 5-methylbarbituric acid 
• 132774-43-7 1-<(benzyloxy)methyl>-6-(phenylthio)thymine 
• 123027-56-5 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine 

Downstream Products

• 157401-04-2 5-Methyl-1-((E)-3-phenyl-allyl)-6-phenylsulfanyl-1H-pyrimidine-2,4-dione 
• 157401-07-5 5-Methyl-6-phenylsulfanyl-1-((E)-3-thiophen-2-yl-allyl)-1H-pyrimidine-2,4-dione 
• 157401-05-3 5-Methyl-6-phenylsulfanyl-1-((E)-3-pyridin-3-yl-allyl)-1H-pyrimidine-2,4-dione 
• 157401-06-4 1-((E)-3-Furan-2-yl-allyl)-5-methyl-6-phenylsulfanyl-1H-pyrimidine-2,4-dione 
• 136160-21-9 1-butyl-6-(phenylthio)thymine 
• 136160-20-8 1-ethyl-6-(phenylthio)thymine 
• 136160-19-5 1-methyl-6-(phenylthio)thymine 
• 144410-28-6 dimethyl-6-(phenylthio)thymine 

Relevant articles and documents

Functionalization of unprotected uracil derivatives using the halogen - Magnesium exchange

The reaction of commercially available 5-iodouracil with 2 equiv of MeMgCl in the presence of LiCl, followed by the addition of i-PrMgCl-LiCl, provides the corresponding trimagnesiated species, which reacts with various electrophiles to give selectively 5

Synthesis and anti-HIV activity of novel N-1 side chain-modified analogs of 1-[(2-hydroxyethoxy)methyl]-6-(phenylthio)thymine (HEPT)

A series of 33 N-1 side chain-modified analogs of 1-[(2- hydroxyethoxy)methyl]-6-(phenylthio)thymine (1, HEPT) were synthesized and evaluated for their anti-HIV-1 activity. In particular, the influence of substitution of the terminal hydroxy group of the acyclic structure of HEPT and the structural rigidity of this side chain were investigated. Halo (7, 8), azido (9), and amino (10-15) derivatives were synthesized from HEPT via the p-tosylate derivative 6. Acylation of the primary amine 15 afforded the amido analogs 16-20. The diaryl derivatives 26-29 were prepared by reaction of HEPT, or of the 6-(2-pyridylthio) analog 23, with diaryl disulfides in the presence of tri-n-butylphosphine. Compounds 39-41, in which the N-1 side chain is rigidified by incorporation of an E-configured double bond, were obtained by palladium(0)-catalyzed coupling of several different 6- (arylthio)uracil derivatives (37, 38) with allyl acetates 33. Compounds 13, 40a,c,d,f, and 41, incorporating an aromatic ring at the end of the acyclic side chain, were found to be more potent than the known diphenyl-substituted HEPT analog BPT (2), two of them, 40c,d, being 10-fold more active.

Pyrimidine derivatives and anti-viral agent containing the same as active ingredient thereof

The disclosure concerns pyrimidine derivatives represented by the following general formulas [I] and [I'] and having antiviral activity, particularly antiretroviral activity such as anti-HIV activity: STR1 and pharmaceutical compositions having antiviral

Synthesis of deoxy analogs of HEPT involving a palladium (0) catalyzed coupling

Deoxy analogs of HEPT (4-7) were prepared by Pd(0) catalyzed coupling between 6-(phenylthio)thymine and cinnamyl acetate or 3-(heteroaryl) allyl acetates.

Synthesis and Antiviral Activity of Deoxy Analogs of 1--6-(phenylthio)thymine (HEPT) as Potent and Selective Anti-HIV-1 Agents

The effect of substitution in the acyclic structure of 1--6-(phenylthio)thymine (HEPT) on anti-HIV-1 activity was investigated by synthesizing a series of deoxy analogs and related compounds.Preparation of 1-(2-alkyloxyethoxy)met