Ethyl orthopropionate → HCID 13393635, compound

HRID 485501Notes

Reaction equation

HRID 485501 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 (0.035 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. Recrystallizations from ethyl acetate-hexane and ethyl acetate-cyclohexane provided 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-f45cbea3306d4a59ae2922457c5bded3
Source dataset
uspto-grants-1985_08
Patent number
US04536579

Reaction notes

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