Iodoethane → HCID 21537681, compound

HRID 1076559Notes

Reaction equation

HRID 1076559 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([OH:14])=[C:10]([C:12]#[N:13])[N:11]=[C:6]2[CH:5]=[N:4]1)[CH3:2].[Na].[CH2:16](I)[CH3:17]>C(O)C>[CH2:16]([O:14][C:9]1[N:8]=[C:7]2[N:3]([CH2:1][CH3:2])[N:4]=[CH:5][C:6]2=[N:11][C:10]=1[C:12]#[N:13])[CH3:17]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 5360545SodiumHCID 178463030HCID 178463030, compound

Product 1

HCID 21537681HCID 21537681, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

18.9 g. of 1-ethyl-6-hydroxy-1H-pyrazolo[3,4-b]-pyrazine-5-carbonitrile (0.1 mol.) are added to a solution of 2.3 g. of sodium (0.1 mol.) in 500 ml. of absolute ethanol and the mixture is stirred for 30 minutes at room temperature. Then the alcohol is distilled off in vacuo and the sodium salt is dissolved in dry dimethylformamide. Then 23.5 g. of ethyl iodide (0.15 mol.) are added and the solution is heated in an autoclave at 120° for 5 hours. After the dimethylformamide is removed in vacuo, the residual 6-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyrazine-5-carbonitrile (19.1 g.) is recrystallized from hexane, yield 17 g. (78%), m.p. 73°-74°.

Workup

  1. distillationThen the alcohol is distilled off in vacuo
  2. dissolutionthe sodium salt is dissolved in dry dimethylformamide
  3. temperaturethe solution is heated in an autoclave at 120° for 5 hours
  4. customAfter the dimethylformamide is removed in vacuo
  5. customthe residual 6-ethoxy-1-ethyl-1H-pyrazolo[3,4-b]pyrazine-5-carbonitrile (19.1 g.) is recrystallized from hexane, yield 17 g

Sources & evidence

ORD record
ord-5ad729be47fd4dd1b24ba30f9c6d45c5
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

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