Ethyl orthopropionate → HCID 13393635, compound
Reaction equation
[CH2:1]([C:3]1[N:8]=[C:7]([N:9]2[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]2)[CH:6]=[C:5]([NH:16][NH2:17])[N:4]=1)[CH3:2].[C:18](OCC)(OCC)(OCC)[CH2:19][CH3:20]>>[CH2:19]([C:20]1[N:4]2[C:3]([CH2:1][CH3:2])=[N:8][C:7]([N:9]3[CH2:14][CH2:13][N:12]([CH3:15])[CH2:11][CH2:10]3)=[CH:6][C:5]2=[N:16][N:17]=1)[CH3:18]Participants
3
Procedure
A mixture of 8.3 g (0.045 mole) of 2-ethyl-6-hydrazinyl-4-(4-methyl-1-piperazinyl)pyrimidine and 75 ml of triethyl orthopropionate was heated at reflux for 48 hours. After cooling the mixture was evaporated in vacuo. Diethyl ether was added to the residue and the mixture was cooled. The precipitate was collected by filtration to provide 4.5 g (37%) of 3,5-diethyl-7-(4-methyl-1-piperazinyl)-1,2,4-triazolo[4,3-c]pyrimidine. Recrystallization from ethyl acetate-hexane and then from ethyl acetate-cyclohexane provided a white crystalline product, m.p. 128°-131° C. Analysis for C14H22N6 : Calculated: %C, 61.3; %H, 8.1; %N, 30.6; Found: %C, 59.8; %H, 8.2; %N, 30.1. The structural assignment was confirmed by nuclear magnetic resonance and infrared spectral analyses.