Ethyl orthopropionate → HCID 13393635, compound

HRID 1589634Notes

Reaction equation

HRID 1589634 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

Reactant 2

HCID 66995Ethyl orthopropionateHCID 133936142-Ethyl-6-hydrazinyl-4-(4-methyl-1-piperazinyl)pyrimidine

Product 1

HCID 13393635HCID 13393635, compoundYield 37%

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.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 48 hours
  3. temperatureAfter cooling the mixture
  4. customwas evaporated in vacuo
  5. additionDiethyl ether was added to the residue
  6. temperaturethe mixture was cooled
  7. filtrationThe precipitate was collected by filtration

Sources & evidence

ORD record
ord-4c21998076f04b229cd6cc2b171e743b
Source dataset
uspto-grants-1986_02
Patent number
US04572910

Reaction notes

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