445040-58-4

Upstream product

• 124-40-3 dimethyl amine 
• 33097-11-9 4,6-dichloro-2-methylsulfanylpyrimidine-5-carboxyaldehyde 
• 6299-25-8 4,6-Dichloro-2-(methylthio)pyrimidine 
• 68-12-2 N,N-dimethyl-formamide 

Downstream Products

• 1393456-95-5 (4-chloro-6-dimethylamino-2-methylsulfanylpyrimidin-5-yl)(4-chlorophenyl)methanol 
• 1393456-94-4 (4-chloro-6-dimethylamino-2-methylsulfanylpyrimidin-5-yl)phenylmethanol 
• 1393456-96-6 (4-chloro-6-dimethylamino-2-methylsulfanylpyrimidin-5-yl)(4-methoxyphenyl)methanol 
• 1393457-04-9 C₂₂H₁₈ClN₃OS₂ 
• 1393457-05-0 C₁₇H₁₆N₄OS₂ 
• 1393457-06-1 C₂₁H₂₅N₃O₃S₂ 
• 1104638-78-9 4-dimethylamino-2-methylthio-6-phenylethynylpyrimidine-5-carbaldehyde 

Relevant academic research and scientific papers

New method for the synthesis of thieno[2,3-d]pyrimidines

The reaction of 5-formyl-4-thiocyanatopyrimidines with nitromethane was studied under various conditions. The reaction was found unexpectedly to proceed with closure of a thiophene ring to give thieno[2,3-d]pyrimidines. The use of ammonium acetate as the catalyst leads to a side reaction involving closure of an isothiazole ring to give isothiazolo[5,4-d]pyrimidines. X-ray diffraction crystallographic analysis was used to confirm the structure of thieno[2,3-d]pyrimidine.

Synthesis of 5,6-disubstituted thieno[2,3-d]pyrimidines from 4-chloropyrimidines

Facile reaction sequences for the preparation of 5,6-disubstituted thieno[2,3-d]pyrimidines starting with 4-chloropyrimidines have been developed. 4-Chloro-6-methoxypyrimidines were aroylated at the 5-positions via lithiation with LDA and subsequent treatment with benzaldehyde or N-methoxy- Nmethylbenzamides to give aryl(4-chloro-6-methoxypyrimidin-5-yl)methanones. These pyrimidinyl ketones were transformed in one-pot into 5,6-disubstituted 4-methoxythieno[2,3-d]pyrimidines by a successive treatment with sodium sulfide, BrCH2EWGs, and sodium hydride. Lithiation of 4,6-dichloro-2-(methylsulfanyl) pyrimidine at the 5-position was followed by treatment with tertiary formamides to give 4-chloro-6-(dialkylamino)pyrimidine-5-carboxaldehydes, which could be transformed into 5,6-disubstituted 4-(dialkylamino)thieno[2,3-d]pyrimidines via aryl[4-chloro-6-(dialkylamino)-pyrimidin-5-yl]methanones using the same one-pot thiophene ring forming sequence.

Synthesis of isoxazolo [3,4-d]pyrimidines from 6-chloropyrimidine-5-carbaldehydes

4-Dialkylamino-6-chloro-2-methylthiopyrimidine-5-carbaldehydes with sodium azide in dimethylformamide underwent ring closure reaction to form the corresponding isoxazolo[3,4-d]pyrimidines.