Water → 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyrimidine

HRID 1043690

Reaktionsgleichung

Reaktionsgleichung von HRID 1043690
[H-].[Na+].[CH3:3][C:4]1[CH:8]=[C:7]([CH3:9])[NH:6][N:5]=1.Cl[C:11]1[N:16]=[CH:15][CH:14]=[CH:13][N:12]=1.O>C1COCC1>[N:12]1[CH:13]=[CH:14][CH:15]=[N:16][C:11]=1[N:5]1[C:4]([CH3:3])=[CH:8][C:7]([CH3:9])=[N:6]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 62103,5-DimethylpyrazoleHCID 24758Sodium hydrideHCID 744042-Chloropyrimidine

Produkt 1

HCID 304649062-(3,5-dimethyl-1H-pyrazol-1-yl)pyrimidineAusbeute 69 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

NaH (0.594 g, 14.84 mmol) was suspended in THF (10 mL), and 3,5-dimethylpyrazole (1.091 g, 11.35 mmol) was slowly added and stirred for one hour at room temperature. 2-Chloropyrimidine (1 g, 8.73 mmol) was slowly added to the mixture and refluxed for three hours. Completion of the reaction was confirmed by TLC, and then water (5 mL) was added to the mixture. The solvent was distilled off and the residue was extracted with ethyl acetate twice. The organic phase was washed with saturated brine and dried over magnesium sulfate. The solvent was then distilled off and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2→ethyl acetate) to give 1.05 g of the title compound (yield 69%).

Aufarbeitung

  1. temperaturerefluxed for three hours
  2. distillationThe solvent was distilled off
  3. extractionthe residue was extracted with ethyl acetate twice
  4. washThe organic phase was washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. distillationThe solvent was then distilled off
  7. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:2→ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-80403708ca76439d9aab5d6698a31937
Quelldatensatz
uspto-grants-2013_10
Patentnummer
US08563552B2

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