154867-11-5

Basic information

• Product Name: ethyl 5-(4-chlorophenyl)-2-[4-(dimethylamino)benzylidene]-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• Synonyms: ethyl 5-(4-chlorophenyl)-2-[4-(dimethylamino)benzylidene]-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate
• CAS NO: 154867-11-5
• Molecular Formula: C25H24ClN3O3S
• Molecular Weight: 481.99436
• Mol File: 154867-11-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: ethyl 5-(4-chlorophenyl)-2-[4-(dimethylamino)benzylidene]-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate(CAS DataBase Reference)
• NIST Chemistry Reference: ethyl 5-(4-chlorophenyl)-2-[4-(dimethylamino)benzylidene]-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate(154867-11-5)
• EPA Substance Registry System: ethyl 5-(4-chlorophenyl)-2-[4-(dimethylamino)benzylidene]-7-methyl-3-oxo-2,3-dihydro-5H-[1,3]thiazolo[3,2-a]pyrimidine-6-carboxylate(154867-11-5)

Safety Data

• Hazardous Substances Data: 154867-11-5(Hazardous Substances Data)

Upstream product

• 154866-92-9 ethyl 4-(4-chlorophenyl)-1,2,3,4-tetrahydro-6-methyl-2-thioxopyrimidine-5-carboxylate 
• 79-11-8 chloroacetic acid 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 141-97-9 ethyl acetoacetate 
• 104-88-1 4-chlorobenzaldehyde 
• 2826-28-0 p-(N-dimethylamino benzylidene) malononitrile 
• 181058-43-5 ethyl 5-(4-chlorophenyl)-7-methyl-3-oxo-3,5-dihydro-2H-thiazolo[3,2-a]pyrimidine-6-carboxylate 
• 154866-92-9 ethyl 6-methyl-4-(4-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxylate 

Relevant articles and documents

Synthesis and radiation stability of novel thiazolopyrimidines with expected antifungal activity

A number of thiazolopyrimidines (II-VII) were prepared through interaction of 6-methyl-4(4′-chlorophenyl)-2-thioxo-1,2,3,4-tetrahydropyrimidine-5- carboxylic acid ethyl ester (Ia) with many reagents. The antifungal activity of all prepared compounds have been determined using Dithane M-45 as a standard fungicide. Some compounds showed a high fungicidal activity equivalent to that of the standard towards Aspergillus niger and Aspergillus ochraceus. Also some biologically active compounds were subjected to gamma irradiation and the structures are stable.

A convenient synthesis of thiazolopyrimidines, thiazolodipyrimidines and heterocyclothiazolopyrimidines

Ethyl 4-aryl-6-substituted-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carboxyla tes 1 reacted with bromomalononitrile (2) to give ethyl 3-amino-5-aryl-2-cyano-7-substituted-5H-thiazolo[3,2-a]pyrimidine-6-ca rboxylates 3. The latter compounds reacted with formic acid, hydroxylamine hydrochloride and with formamide to give 9H-3,4-dihydrothiazolo[3,2-a:4,5-b]dipyrimidine-8-carboxylates 5, 1H,8H-pyrazolo[3,4-d]thiazolo[3,2-a]pyrimidine-7-carboxylates 8 and 2,7-diaminothiazolo[4,5-d]pyrimidine (7), respectively. Compounds 1b,e reacted with chloroacetyl chloride to yield ethyl 5-aryl-3-oxo-7-substituted-2,3-dihydro-5H-thiazolo[3,2-a]pyrimidine-6- carboxylates 9a,b which coupled with arenediazonium chlorides to give the corresponding 2-arylhydrazone derivatives 10a,b. Compound 9a adds α-cyanocinnamonitriles 12a-c to yield ethyl 2-amino-4-aryl-3-cyano-9-(4-methoxyphenyl)-7-methyl-4H,9H-pyrano[2,3-d ]thiazolo[3,2-a]pyrimidine-8-carboxylates 13a-c. Refluxing 1b-d with phenacyl bromide produced ethyl 5-aryl-7-methyl-3-phenyl-5H-thiazolo[3,2-a]pyrimidine-6-carboxylates 14a-c.