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

HRID 65700Notes

Reaction equation

HRID 65700 reaction equation
[CH2:1]([N:3]1[C:7]2[N:8]=[CH:9][C:10]3[C:11](=[O:20])[NH:12][C:13]4[N:14]([N:16]=[C:17]([CH3:19])[CH:18]=4)[C:15]=3[C:6]=2[CH:5]=[N:4]1)[CH3:2].[H-].[Na+].[CH3:23]I>COCCOCCOC>[CH3:19][C:17]1[CH:18]=[C:13]2[N:12]([CH3:23])[C:11](=[O:20])[C:10]3[CH:9]=[N:8][C:7]4[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]=4[C:15]=3[N:14]2[N:16]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1358394108-ethyl-2-methyl-4-H-pyrazolo[1,5-a]pyrazolo[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one

Product 1

HCID 227574542,4-dimethyl-8-ethyl-4H-pyrazolo[1,5-a]pyrazolo[4', 3': 5,6]pyrido[3,4-e]pyrimidin-5(8H)-one

Reagents, catalysts & solvents 1

HCID 8150DiglymeSolvent

Procedure

2.7 g. of 8-ethyl-2-methyl-4H-pyrazolo[1,5-a]pyrazolo-[4',3':5,6]pyrido[3,4-e]pyrimidin-5(8H)-one (0.01 mol.) are added to a suspension of 0.03 g. of sodium hydride in 50 ml. of diethylene glycol dimethyl ether at reflux temperature. The temperature is maintained for one hour and then lowered to 120°. 2.8 g. of methyl iodide are added and heating is continued for 10 hours. The precipitated sodium iodide is filtered off, the solution evaporated to dryness and the residue recrystallized from ethyl-acetate, yield 1.9 g. (68%); m.p. 206°-207°.

Workup

  1. temperatureThe temperature is maintained for one hour
  2. customlowered to 120°
  3. temperatureheating
  4. filtrationThe precipitated sodium iodide is filtered off
  5. customthe solution evaporated to dryness
  6. customthe residue recrystallized from ethyl-acetate, yield 1.9 g

Sources & evidence

ORD record
ord-7740ebeeaa2d4addbbf820bb3b2bbe51
Source dataset
uspto-grants-1978_12
Patent number
US04128645

Reaction notes

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