66348-67-2

Basic information

• Product Name: Pyrimidine, 2-[(phenylmethyl)thio]-
• CAS NO: 66348-67-2
• Molecular Formula: C11H10N2S
• Molecular Weight: 202.28
• Mol File: 66348-67-2.mol

Chemical Properties

• CAS DataBase Reference: Pyrimidine, 2-[(phenylmethyl)thio]-(CAS DataBase Reference)
• NIST Chemistry Reference: Pyrimidine, 2-[(phenylmethyl)thio]-(66348-67-2)
• EPA Substance Registry System: Pyrimidine, 2-[(phenylmethyl)thio]-(66348-67-2)

Safety Data

• Hazardous Substances Data: 66348-67-2(Hazardous Substances Data)

Upstream product

• 1589-82-8 phenylmagnesium bromide 
• 89283-87-4 2-thiocyanatopyrimidine 
• 131242-36-9 2-sulfanylpyrimidine 
• 100-39-0 benzyl bromide 
• 14080-23-0 2-cyanopyrimidine 
• 100-53-8 phenylmethanethiol 
• 55796-74-2 (benzylsulfanyl)methanimidamide hydrobromide 
• 1722-12-9 2-chloropyrimidine 
• 100-51-6 benzyl alcohol 
• 4595-60-2 2-bromopyrimidine 
• 1356160-96-7 C₅H₆N₄S 
• 100-44-7 benzyl chloride 

Downstream Products

• 122080-51-7 benzyl 2-pyrimidinyl sulfoxide 
• 144708-17-8 2-<(phenylmethyl)sulfonyl>pyrimidine 
• 103-30-0 (E)-1,2-diphenyl-ethene 
• 1608-31-7 (cyclohexylidenemethyl)benzene 
• 62839-72-9 (Z)-1-(dec-1-enyl)benzene 
• 62839-71-8 (E)-1-phenyl-1-decene 
• 847778-94-3 CF₃O₃S^(1-)*C₁₂H₁₃N₂S⁽¹⁺⁾ 
• 350-50-5 benzyl fluoride 

Relevant articles and documents

Decyanative Cross-Coupling of Cyanopyrimidines with O-, S-, and N-Nucleophiles: A Route to Alkoxylpyrimidines, Aminopyrimidines and Alkylthiopyrimidines

The transition metal-free cross-coupling reactions of cyanopyrimidines with aliphatic alcohols, thiols (or S-alkylisothiourea salts) and amines, giving the corresponding alkoxylpyrimidines, aminopyrimidines, and alkylthiopyrimidines, are reported. Prelimi

Promoting Effect of Crystal Water Leading to Catalyst-Free Synthesis of Heteroaryl Thioether from Heteroaryl Chloride, Sodium Thiosulfate Pentahydrate, and Alcohol

It is observed the crystal water in sodium thiosulfate pentahydrate (Na2S2O3·5H2O) can promote its multicomponent reaction with heteroaryl chlorides and alcohols, providing a facile, green, and specific synthesis of unsymmetrical heteroaryl thioethers via one-step formation of two C-S bonds under catalyst-, additive-, and solvent-free conditions. Mechanistic studies suggest that the crystal water in Na2S2O3·5H2O is crucial in generating the key thiol intermediates and byproduct NaHSO4, which then catalyzes the dehydrative substitution of alcohols with thiols to afford thioethers.

Efficient Generation of C–S Bonds via a By-Product-Promoted Selective Coupling of Alcohols, Organic Halides, and Thiourea

A metal- and base-free three-component coupling of alcohols, heteroaryl halides, and thiourea has been developed for direct and selective synthesis of heteroaryl thioethers. This method can be easily scaled up to the gram scale and extended to dialkyl thioethers, heteroaryl selenides, benzothiazoles, and some antimycobacterially-active thioethers. Mechanistic studies revealed that a by-product-promoted in situ C–O activation of alcohols to more reactive alkyl halides and slow release of the thiol and alkyl halide intermediates are the key to the high selectivity and success of the reaction. (Figure presented.).

Copper-Catalyzed Aerobic Formation of Unstable Sulfinyl Radicals for the Synthesis of Sulfinates and Thiosulfonates

Copper-catalyzed aerobic coupling of thiols and alcohols affords sulfinates and thiosulfonates. These products are assumed to form via sulfinyl radicals which are not commonly found in oxidative coupling reactions of thiols. A reaction mechanism involving sulfinyl radicals is proposed, and mass and electron paramagnetic resonance (EPR) experimental results are provided.

One-pot Metal-free Synthesis of Benzyl Alkyl Sulfides

The synthesis of sulfides is important in various fields. This paper reports an efficient, odorless, and viable protocol for the base-mediated synthesis of benzyl alkyl sulfides using thiourea. The reactions were carried out under transition-metal-free co

Modification of thionucleobases in ionic liquids

A simple method was established for the preparation of thio-substituted thionucleobases using room temperature ionic liquids (RTILs) such as 1-butyl-3-methylimidazolium trifluoroacetate [BMIM]+[CF3COO]- and 1-methoxyethyl-3-methylimidazolium trifluoroacetate [MeOEtMIM]+[CF3COO]- as solvents and catalysts without any other catalyst. These reactions proceeded efficiently in RTILs with excellent yield of products. RTILs can be recycled and reused effectively without further purification.

One-pot palladium-catalyzed borrowing hydrogen synthesis of thioethers

Palladium on magnesium oxide is able to allow a one-pot reaction to synthesize thioethers from thiols and aldehydes formed in situ from the respective alcohol by means of a borrowing hydrogen method. The reaction is initiated by dehydrogenation of the alcohol to give a palladium hydride intermediate and an aldehyde. The latter reacts with a thiol involving most probably the intermediacy of a thionium ion RCHi￡S+R, which can be reduced in situ by the metal hydride to afford thioethers. Lending support: Palladium nanoparticles on MgO catalyze the synthesis of thioethers from thiols and aldehydes formed in situ from alcohols by means of the borrowing hydrogen method (see scheme). Dehydrogenation of the alcohol gives a palladium hydride intermediate and an aldehyde. The latter reacts with a thiol through a thionium ion, which is reduced by the metal hydride to afford thioethers.

Microwave-promoted "one-Pot" synthesis of 4- nitrobenzylthioinosine analogues using thiourea as a sulfur precursor

An efficient one-pot method for the synthesis of various C6-alkylthio-substituted purine nucleosides has been developed under microwave irradiation with good to excellent yields without any metal catalyst (see scheme). This process expands the scope of existing synthetic methodologies and was further successfully applied for synthesis of the biologically important compound 4-nitrobenzylthioinosine (NBTI).

COMPOUNDS AND KITS FOR PREPARING IMAGING AGENTS AND METHODS OF IMAGING

Compounds that include a targeting moiety bound to a regioselective leaving group are useful for preparing imaging agents. The imaging agents can be isolated from by-products derived from the leaving group based on differences in the chemical attributes (e.g., net charge or polarity) of the molecules or physical attributes of the molecules through the use of a solid support. Methods of producing an imaging agent include the steps of providing a compound that includes a targeting moiety bound to a support via a linker group that contains a site for regioselective substitution of a detectable species, contacting the compound with a solution containing the detectable species, and recovering the imaging agent. Kits which include a first container (5) having therein a solution (31) containing a detectable species and a second container (2) having therein a compound that includes a targeting moiety bound to a support (30) via a leaving group that contains a site for regioselective substitution of the detectable species are also useful for preparing imaging agents.

Antimycobacterial Agents. 1. Thio Analogues of Purine

Thio analogues of purine, pyridine, and pyrimidine were prepared based on the initial activity screening of several analogues of these heterocycles against Mycobacterium tuberculosis (Mtb). Certain 6-thio-substituted purine analogues described herein showed moderate to good inhibitory activity. In particular, two purine analogues 9-(ethylcarboxymethyl)-6-(decylthio)-9H-purine (20) and 9-(ethylcarboxymethyl)-6-(dodecylthio)-9H-purine (21) exhibited MIC values of 1.56 and 0.78 μg/mL respectively against the Mtb H37Rv strain. N9-Substitution apparently enhances the antimycobacterial activity in the purine series described herein.