21575-85-9

Upstream product

• 81107-82-6 [1-Phenyl-prop-(Z)-ylidene]-trimethylsilanyl-amine 
• 21575-84-8 4-chloro-2-dimethylamino-5-methyl-6-phenylpyrimidine 

Downstream Products

• 129995-82-0 2-dimethylamino-4-<2-ethoxycarbonyl-hydrazido>-5-methyl-6-phenyl pyrimidine 
• 129995-80-8 3-anilino-5-dimethylamino-8-methyl-7-phenyl-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-81-9 3-(2-chloro)-anilino-5-dimethylamino-8-methyl-7-phenyl-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-76-2 C₁₆H₂₂N₆ 
• 129995-85-3 3,5-bis-(dimethylamino)-8-methyl-7-phenyl-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-78-4 4--2-dimethylamino-5-methyl-6-phenylpyrimidine 
• 129995-71-7 5-dimethylamino-8-methyl-3-morpholino-7-phenyl-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-79-5 2-dimethylamino-5-methyl-6-phenyl-4-(trifluoromethyl-dimethylaminomethylenehydrazino)-pyrimidine 
• 129995-73-9 3-benzylamino-5-dimethylamino-8-methyl-7-phenyl-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-86-4 5-dimethylamino-8-methyl-7-phenyl-3-pyrrolidino-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-87-5 5-dimethylamino-8-methyl-7-phenyl-3-piperidino-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-72-8 5-dimethylamino-8-methyl-3-perhydroazepinyl-7-phenyl-(1,2,4)-triazolo-<4,3-c>-pyrimidine 
• 129995-84-2 C₁₇H₂₀ClN₅O₂ 
• 129995-83-1 5-dimethylamino-2-ethoxycarbonyl-8-methyl-7-phenyl-(1,2,4)-triazolo-<1,5-c> pyrimidine 

Relevant academic research and scientific papers

A mild and regiospecific synthesis of 3-amino substituted triazolo-[4,3-c]-pyrimidines by cyclisation of 4-hydrazinopyrimidines with iminium chlorides and with N-aryl phosgenimines

Phosgeniminium chloride (PI) 1a permits the regiospecific synthesis of 3-dimethylaminotriazolo-[4,3-ch-pyrimidine 8a from the corresponding 4-hydrazinopyrimidine 5 without Dimroth type isomerisation into its [1,5-c isomer. This synthesis has been extended to the cyclic phosgeniminium salts 1b-e and to the N-aryl phosgenimines (aryl isocyanide dichlorides) 18a,b. The triazolopyrimidine structure was confirmed by an X-ray diffraction analysis of derivative 8d. When the Vilsmeier salt 10, tetramethylurea dichloride 11 or dimethyl(2,2,2-trifluoro-1,1-dichloroethyl)amine 12 were used as the electrophilic reagents, 4-methylenehydraiinopyrimidines 13, 14 and 15 respectively were isolated. Thermolysis of 13 yielded with the same regiospecificity 3-unsubstituted triazolo-[4,3-c-pyrimidine 16. This compound could be rearranged to 17 in a separate step. Chlorination of hydrazidopyrimidine 20 in refluxing POCl3 led to the isomerised triazolo-[1, 5-ch-pyrimidine 22, as ascertained by X-ray diffraction and 13C-nmr analysis.