154366-93-5

Upstream product

• 2228-12-8 6-methyl-4-phenyl-2-thioxo-1,2-dihydropyrimidine-5-carbonitrile 
• 107-14-2 chloroacetonitrile 
• 2228-12-8 4-methyl-6-mercapto-2-phenylpyrimidine-5-carbonitrile 
• 216776-76-0 6-Fluoro-4-methyl-2-phenyl-thieno[2,3-d]pyrimidin-5-ylamine 
• 216776-67-9 (5-Cyano-6-methyl-2-phenyl-pyrimidin-4-ylsulfanyl)-fluoro-acetic acid ethyl ester 
• 532-55-8 Benzoyl isothiocyanate 

Downstream Products

• 154366-96-8 N-(2-Cyan-4-methyl-6-phenyl-thieno<2,3-d>pyrimid-3-yl)-oxalamid-saeureethylester 
• 154366-94-6 4-Methoxy-9-methyl-7-phenyl-thieno<2,3-d:4,5-d'>dipyrimidin-2-carbonsaeuremethylester 
• 209682-32-6 9-Methyl-7-phenyl-1H-thieno[2,3-d;4,5-d']dipyrimidine-2,4-dithione 
• 209683-11-4 4-Imino-9-methyl-7-phenyl-4H-thieno[2,3-d;4,5-d']dipyrimidin-3-ylamine 

Relevant academic research and scientific papers

Synthesis and reactions of some new thienopyrimidines

4-Methyl-6-mercapto-2-phenylpyrimidine-5-carbonitrile (1) was reacted with different halo compounds, namely ethylchloroacetate, chloroacetone, bromoacetanilide, p-chlorobromoacetanilide, and p-methoxy chloroacetanilide in ethanol in the presence of sodium acetate yielded the corresponding S-alkylated derivatives (2a-e). The latter compounds underwent cyclization into thienopyrimidines (4a-e) upon treatment with sodium ethoxide in ethanol. The reaction of (4a) with hydrazine hydrate led to the formation of 5-amino-4-methyl-2-phenylthieno[2,3-d]pyrimidine-2-carbohydrazide (5). Compound (5) was reacted with a variety of reagents to produce other new thienopyrimidines as well as oxadiazolylthienopyrimidines (6, 11).

Synthesis of some pyrimidothienopyrimidine derivatives

The pyrimidothienopyrimidines 5 and 6 have been synthesized via the reaction of compounds 4a, b with CS2 and were further transformed to related fused heterocyclic systems.

An easy direct conversion of pyridine- and pyrimidine-thiones into multi-fused heterocyclic compounds

The reaction of azine-thiones with ethyl chlorofluoroacetate afforded 2- fluorothienoazines. The latter underwent self-condensation and gave multi- fused heterocyclic compounds. A wide range of unique heterocycles could be obtained on treatment of 2-fluorothienoazines with nitrogen nucleophilic reagents. The reactivity of the pyrimidine-thiones towards a variety of electrophilic reagents was studied. Chemical and spectroscopic evidence of the newly synthesized compounds are described.

Synthesis of 4-methyl-6-phenyl-thieno[2,3-d]pyrimidines with a formamidino or an oxalamido carbonic acid residue and antianaphylactic activity

3-Amino-4-methyl-6-phenyl-thieno[2,3-d]pyrimidine-2-carbonic acid alkylesters 1a, b were hydrolyzed to the potassium salt of the carbonic acid 2. Cyclization of 2 with acetanhydride yielded the tricyclic 1,3-oxazinone derivative 4. This compound reacted with pyrrolidine by different conditions of reaction to give the bisamide 7, the acetamidino carbonic acid 5 and their decarboxylated product 6. Compound 1a yielded with Vilsmeier reagens the formamidino compound 3. 3-Amino-thieno[2,3-d]pyrimidin-2-carbonitrile gave under different conditions of reaction with oxalic acid diethylester or with oxalic acid ethylester chloride the tetracyclic 4-methoxy-9-methyl-7-phenyl-thieno[2,3-d:4,5-d']dipyrimidine-2-carboni c acid methylester 10 or the N-(2-cyano-4-methyl-6-phenyl-thieno[2,3-d]pyrimid-3-yl)oxalamidic ethylester 12. These compounds were hydrolyzed to give the carbonic acids 11 and 13. Some of the synthesized substances showed an antianaphylactic activity.