77752-56-8

Upstream product

• 934-87-2 S-phenyl thioacetate 
• 75-05-8 acetonitrile 
• 80781-09-5 2,6-dimethyl-4-<(ethoxymethylene)amino>pyrimidine 
• 461-98-3 4-amino-2,6-dimethylpyrimidine 
• 930-69-8 sodium thiophenolate 
• 80781-13-1 1-(2,6-dimethyl-4-pyrimidyl)-4-tosylimidazole 
• 4472-45-1 4-chloro-2,6-dimethylpyrimidine 
• 108-98-5 thiophenol 

Downstream Products

• 77752-49-9 2,6-dimethyl-4-phenylsulfonylpyrimidine 
• 77752-58-0 2,6-dimethyl-4-(2-oxocyclohexyl)pyrimidine 
• 65845-63-8 2-(2,6-dimethyl-pyrimidin-4-yl)-1-phenyl-ethanone 
• 6622-92-0 2,6-dimethyl-1H-pyrimidin-4-one 

Relevant academic research and scientific papers

The reaction of thioesters with nitriles. A new synthetic approach to the preparation of substituted 4-alkylthio- and 4-arylthiopyrimidine derivatives

S-Alkyl and S-aryl thioesters react with nitriles in the presence of triflic anhydride to form substituted 4-alkylthio- and 4-arylthiopyrimidines. However, when methyl thiocyanate is used as nitrile, dithioimidocarbonates are formed. A mechanism to explain these differences is postulated.

Nucleophilic Displacement of Primary Amino Groups via 1-Substituted 4-Tosylimidazoles

Two methods are discribed for the replacement of primary amino groups, situated either α or γ to a heterocyclic nitrogen atom, by ethoxy, alkylthio, and arylthio substituents, by Wittig reagents, and by hydrogen.Both methods involve transformation of the primary amino group into a nucleofugic pendant heterocycle.The first converts the primary amino group into a 5-phenyl-1-tetrazolyl substituent by benzoylation, formation of the imidoyl chloride, and reaction with sodium azide, while the second converts the primary amino group into a 1-(4-tosylimidazolyl) substituent by reaction with triethyl orthoformate and acid to give the (ethoxymethylene)amino derivative, which is then condensed with tosylmethyl isocyanide (TosMIC) anion.The 1-(4-tosylimidazolyl) substituent is shown to be more susceptible to nucleophilic displacement by a wider range of nucleophiles.