Synthesis and reactions of 6‐methylsulfanyl‐2,4‐dithioxo‐1,2,3,4‐tetrahydropyrimidin‐5‐carbonitrile

Abstract

The synthesis of 6-methylsulfanyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile 4 is described. Compound 4 was reacted with various alkylants. The reaction with chloroacetic acid derivatives results in the formation of thieno[2,3-d]pyrimidines 8. When methyl iodide was used 2,4,6-tris(methylsulfanyl)pyrimidine-5-carbonitrile 5 was obtained. The substitution of the methylsulfanyl groups in compound 5 by several N-nuclophiles leads to amino substituted pyrimidines.

Selective Nucleophilic Substitution Reactions in 2,4,6‐Trisulfanyl‐Substituted Pyrimidine‐5‐carbonitriles by Secondary Amines.

“…Some time ago we published the synthesis of 6-methylsulfanyl-2,4-dithioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitrile from simple starting compounds [2]. In that work we have also reported some results of alkylation reaction with electrophiles like alkyl halides, phenacyl bromides and halogeno acetic acid derivatives.…”

An efficient synthesis of 4‐alkoxy‐5,6‐dihydro‐furo(and ‐thieno)[2,3‐d]pyrimidines using zinc chloride/triethylamine reagent system

“…Owing to the great structural diversity of biologically active fused pyrimidines such as quinazoline derivatives, it is not surprising that the fused pyrimidine ring system has become an important structural component in many pharmaceutical agents. In this context, the synthesis [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15][16] of fused pyrimidine derivatives continues to attract attention due to their biological activities [17][18][19][20][21][22][23][24][25] and provides an interesting challenge. For the reasons given above, we have been interested in the development of the methods for the construction of fused pyrimidines.…”