Potassium Carbonate → 3-(2-methoxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-ylamine

HRID 1062799Notes

Reaction equation

HRID 1062799 reaction equation
[NH2:1][C:2]1[N:6]([CH3:7])[N:5]=[C:4]([OH:8])[C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:22][O:23][CH2:24][CH2:25]Br>CN(C)C=O>[CH3:22][O:23][CH2:24][CH2:25][O:8][C:4]1[C:3]([C:9]2[CH:14]=[CH:13][C:12]([CH3:15])=[CH:11][CH:10]=2)=[C:2]([NH2:1])[N:6]([CH3:7])[N:5]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 1784239155-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol

Product 1

HCID 229997133-(2-methoxyethoxy)-1-methyl-4-(4-methylphenyl)-1H-pyrazol-5-ylamineYield 51.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol (Preparation 3a) (305 mg) was dissolved in dimethylformamide (2 ml), potassium carbonate (622 mg) and 2-bromoethyl methyl ether (208 mg) were added. The reaction was stirred at room temperature for 1.5 hours and then at 50° C. for 12 hours. The solvent was removed under reduced pressure. The crude product was purified on silica (10 g) eluted with a solvent gradient of pentane:ethyl acetate (1:0 to 0:1) to yield the title compound as a white solid (201 mg).

Workup

  1. waitat 50° C. for 12 hours
  2. customThe solvent was removed under reduced pressure
  3. customThe crude product was purified on silica (10 g)
  4. washeluted with a solvent gradient of pentane:ethyl acetate (1:0 to 0:1)

Sources & evidence

ORD record
ord-8678ad1bb3684e38ad9faad6c90b4e43
Source dataset
uspto-grants-2005_11
Patent number
US06962923B2

Reaction notes

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