87693-90-1

Usage

Uses

Used in Pharmaceutical Industry:
METHYL 4-(METHYLTHIO)-6-OXO-2-PHENYL-1,6-DIHYDROPYRIMIDINE-5-CARBOXYLATE is used as a potential active pharmaceutical ingredient for the development of new drugs. Its unique structure and the presence of a sulfur atom and phenyl group may contribute to its pharmacological properties, making it a promising candidate for further research and development in the pharmaceutical field.
Used in Medicinal Chemistry Research:
In the field of medicinal chemistry, METHYL 4-(METHYLTHIO)-6-OXO-2-PHENYL-1,6-DIHYDROPYRIMIDINE-5-CARBOXYLATE serves as a valuable compound for studying its interactions with biological targets and understanding its potential therapeutic effects. Its dihydropyrimidine structure and functional groups may offer insights into the design and synthesis of new drugs with improved efficacy and safety profiles.

InChI:InChI=1/C13H12N2O3S/c1-18-13(17)9-11(16)14-10(15-12(9)19-2)8-6-4-3-5-7-8/h3-7H,1-2H3,(H,14,15,16)

Upstream product

• 55-21-0 benzamide 
• 3490-92-4 methyl 2-cyano-3,3-bis(methylsulfanyl)acrylate 
• 118996-48-8 methyl (Z)-3-benzamido-2-cyano-3-methylthiopropenoate 
• 87693-81-0 methyl 3-N-benzoylamino-2-cyano-3-methylthioacrylate 
• 19607-08-0 methyl 2-methoxycarbonyl-3,3-di(methylsulfanyl)acrylate 
• 1670-14-0 benzamidine monohydrochloride 

Downstream Products

• 87694-03-9 methyl 3,4-dihydro-6-morpholino-2-phenyl-4-oxopyrimidine-5-carboxylate 
• 87694-02-8 methyl 6-cyclohexylamino-3,4-dihydro-2-phenyl-4-oxopyrimidine-5-carboxylate 
• 118996-62-6 methyl 6-anilino-4-methylthio-2-phenylpyrimidine-5-carboxylate 
• 87694-01-7 methyl 6-benzylamino-3,4-dihydro-2-phenyl-4-oxopyrimidine-5-carboxylate 
• 118996-79-5 methyl 3,4-dihydroxy-6-phenylthieno<2,3-d>pyrimidine-6-carboxylate 
• 87694-04-0 methyl 6-anilino-3,4-dihydro-2-phenyl-4-oxopyrimidine-5-carboxylate 
• 118996-73-9 3,4-dihydro-2-phenyl-4,5-dioxo-5H-pyrido<1,2-a>pyrimido<4,5-d>pyrimidine 
• 87694-05-1 5-hydroxy-2-phenylpyrimido<4,5-b>quinolin-4(3H)-one 
• 118996-57-9 methyl 2-phenyl-4-methylsulfonyl-6-oxopyrimidine-5-carboxylate 
• 87905-18-8 6-methylthio-2-phenyl-1,3-diazin-4-one 
• 118996-60-4 methyl 4-chloro-6-methylthio-2-phenylpyrimidine-5-carboxylate 

Relevant academic research and scientific papers

Regioselective Synthesis of Pyrimidines from Ketene Dithioacetals or Alkoxymethylene Compounds

Regioselective cyclizations of the condensation products obtained by the reaction of nitrogen nucleophiles with ketene dithioacetals or alkoxymethylene compounds are reported.Stereoelectronic factors or geometry of the carbon-carbon double bond determine

Synthesis of Pyrimidine Derivatives by the Reaction of Ketene Dithioacetals with Amides

Reactions of methyl 2-cyano-3,3-bis(methylthio)acrylate (1a) with carboxamides 2a-g in the presence of sodium hydride in a mixture of benzene and N,N-dimethylacetamide took place displacement with the methylthio group to give the corresponding methyl 3-N-acylamino-2-cyano-3-(methylthio)acrylates 3a-g which were readily converted to the corresponding pyrimidine derivatives at reflux in methanol in good yields.Reactions of 2-cyano-3,3-bis(methylthio)acrylonitrile (1b) with the carboxamides 2a-f gave directly pyrimidine-5-carbonitrile derivatives 7a-f.Ketene dithioacetals 1a,b smoothly reacted with thioamide 2g or urea 2h,i to give the expected pyrimidine derivatives 9,10a,b.Polyfunctionalized pyrimidines, thus obtained, were also used for the synthesis of fused pyrimidine derivatives.

REACTION OF KETENETHIOACETALS WITH CARBOXAMIDES

Reaction of methyl 2-cyano-3,3-bis(methylthio)-acrylate (1a) with carboxamides in the presence of sodium hydride in a mixture of benzene and N,N-dimethylacetamide gave the corresponding displacement products of methylthio group, methyl 3-(N-alkyl or aryl)carbamoyl-2-cyano-3-(methylthio)-acrylates (3a,b,c,d,e,f,g,h).Refluxing of 3 in methanol gave the corresponding cyclized product, 2-alkyl or 2-aryl-5-methoxycarbonyl-6-methylthio-4(3H)-pyrimidones (4).Compound 3a was allowed to react with amine(morpholine, benzylamine, cyclohexylamine, aniline) to give 4-(substituted amino)-4(3H)-pyrimidone derivatives (6a,b,c,d).