Potassium Carbonate → 2-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetate

HRID 1062780

Reaktionsgleichung

Reaktionsgleichung von HRID 1062780
[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+].[C:22]([O:25][CH2:26][CH2:27]Br)(=[O:24])[CH3:23]>CN(C)C=O.O>[C:22]([O:25][CH2:26][CH2:27][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)(=[O:24])[CH3:23]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 135641-Acetoxy-2-bromoethaneHCID 1784239155-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol

Produkt 1

HCID 222820022-{[5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-yl]oxy}ethyl acetateAusbeute 42,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 5-amino-1-methyl-4-(4-methylphenyl)-1H-pyrazol-3-ol (Preparation 3a) (250 mg) in dimethyl formamide (5 ml) at room temperature was added potassium carbonate (510 mg) and 2-bromoethyl acetate (205 mg), the mixture was stirred for 16 hrs. The reaction was diluted with water (60 ml) and extracted with ethyl acetate (3×30 ml). The organic fractions were combined, washed with water (2×30 ml) and brine (30 ml) and dried over magnesium sulfate, filtered concentrated under reduced pressure. The residue was purified by column chromatography (silica, 30 g) eluted with ethyl acetate:hexane (1:1) to yield the title compound as a white solid (151 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×30 ml)
  2. washwashed with water (2×30 ml) and brine (30 ml)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography (silica, 30 g)
  7. washeluted with ethyl acetate:hexane (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-7c6011bb5ebc44cfac5fedd349445810
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06962923B2

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