Potassium Hydroxide → 1-(2-methoxyethyl)-1H-pyrazol-3-amine

HRID 2244467Notes

Reaction equation

HRID 2244467 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][NH:4][N:3]=1.[OH-].[K+].[CH3:9][O:10][CH2:11][CH2:12]Br>CS(C)=O.[Cl-].[Na+].O>[CH3:9][O:10][CH2:11][CH2:12][N:4]1[CH:5]=[CH:6][C:2]([NH2:1])=[N:3]1

Participants

6

Reactant 3

HCID 14797Potassium HydroxideHCID 809722-Bromoethyl methyl etherHCID 178418806HCID 178418806, compound

Product 1

HCID 451167281-(2-methoxyethyl)-1H-pyrazol-3-amine

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

3-Aminopyrazole (2 g, 23 mmol) were dissolved in 15 ml DMSO. Potassium hydroxide (3.8 g, 69 mmol) was added and the mixture was stirred at room temperature for 30 min. 2-Bromoethyl methyl ether (3.2 g, 23 mmol) was added and stirring was continued at room temperature overnight. The reaction mixture was poured into 100 ml brine and extracted three time with 100 ml ethyl acetate. The organic phases were pooled, dried with sodium sulfate and evaporated. The two regiosomers were separated by flash chromatography and the title compound was obtained as a brown oil (0.824 g, 25%), MS (ISP): m/e=142.1 (M+H+).

Workup

  1. stirringstirring
  2. waitwas continued at room temperature overnight
  3. extractionextracted three time with 100 ml ethyl acetate
  4. dry with materialdried with sodium sulfate
  5. customevaporated
  6. customThe two regiosomers were separated by flash chromatography

Sources & evidence

ORD record
ord-5ade20cb9b9d48ca8a71883819ad243d
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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