Methyl iodide → 8-Ethyl-4-methyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidin-5(8H)-one

HRID 2287144Notes

Reaction equation

HRID 2287144 reaction equation
[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]3[C:11](=[O:19])[NH:12][C:13]4[N:14]([N:16]=[CH:17][N:18]=4)[C:15]=3[C:6]=2[CH:5]=[N:4]1)[CH3:2].[Na].[CH3:21]I>COCCOCCOC>[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]3[C:11](=[O:19])[N:12]([CH3:21])[C:13]4[N:14]([N:16]=[CH:17][N:18]=4)[C:15]=3[C:6]=2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 1355938528-Ethyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]-triazolo[1,5-a]pyrimidin-5(8H)-one

Product 1

HCID 234596128-Ethyl-4-methyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidin-5(8H)-one

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

2.6 g. of 8-ethyl-4H-pyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidin-5(8H)-one (0.01 mol.) are treated with 0.3 g. of sodium in 50 ml. of diethyleneglycol dimethyl ether at reflux temperature with stirring for 30 minutes. After this time, the temperature is lowered to 60° and 3 g. of methyl iodide are added. Stirring and heating is continued for 12 hours. The precipitate of sodium iodide is filtered off and the solvent distilled from the mother liquor. The remaining 8ethyl-4-methyl-4Hpyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidin5(8H)-one is recrystallized from butanol, yield 2 g. (75%); m.p. 208°-210°.

Workup

  1. customis lowered to 60°
  2. stirringStirring
  3. temperatureheating
  4. waitis continued for 12 hours
  5. filtrationThe precipitate of sodium iodide is filtered off
  6. distillationthe solvent distilled from the mother liquor
  7. customThe remaining 8ethyl-4-methyl-4Hpyrazolo[4',3':5,6]pyrido[3,4-e][1,2,4]triazolo[1,5-a]pyrimidin5(8H)-one is recrystallized from butanol, yield 2 g

Sources & evidence

ORD record
ord-0ce8de9a43a047ce93dfd1a791f33d79
Source dataset
uspto-grants-1981_05
Patent number
US04269836

Reaction notes

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