Iodoethane → HCID 53872193, compound

HRID 1076562Notes

Reaction equation

HRID 1076562 reaction equation
[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH3:15])=[C:10]([C:12]([OH:14])=[O:13])[N:11]=[C:6]2[CH:5]=[N:4]1)[CH3:2].[Na].[CH2:17](I)[CH3:18]>C(O)C>[CH2:1]([N:3]1[C:7]2=[N:8][C:9]([CH3:15])=[C:10]([C:12]([O:14][CH2:17][CH3:18])=[O:13])[N:11]=[C:6]2[CH:5]=[N:4]1)[CH3:2]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 5360545SodiumHCID 21537672HCID 21537672, compound

Product 1

HCID 53872193HCID 53872193, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

12.1 g. of 1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid (0.059 mol.) are added to a solution of 1.36 of sodium (0.059 mol.) in 250 ml. of absolute ethanol and is stirred for 30 minutes at room temperature. The alcohol is distilled off in vacuo and the sodium salt is dissolved in 350 ml. of dry dimethylformamide. Then, 14 g. of ethyl iodide (0.88 mol.) are added and the solution is heated in an autoclave at 120° for 10 hours. After the dimethylformamide has been removed in vacuo, the residual 1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid ethyl ester is treated with water, dried at 50° and recrystallized from hexane, yield 9.4 g. (68%), m.p. 64°-65°.

Workup

  1. distillationThe alcohol is distilled off in vacuo
  2. dissolutionthe sodium salt is dissolved in 350 ml
  3. temperaturethe solution is heated in an autoclave at 120° for 10 hours
  4. customAfter the dimethylformamide has been removed in vacuo
  5. additionthe residual 1-ethyl-6-methyl-1H-pyrazolo[3,4-b]pyrazine-5-carboxylic acid ethyl ester is treated with water
  6. customdried at 50°
  7. customrecrystallized from hexane, yield 9.4 g

Sources & evidence

ORD record
ord-5b746ffa36454df98da283762dbb7483
Source dataset
uspto-grants-1976_05
Patent number
US03957782

Reaction notes

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