Hydrochloric Acid → Ethyl 7-amino-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylate

HRID 965998

Reaktionsgleichung

Reaktionsgleichung von HRID 965998
Cl.[C:2]1([CH3:17])[CH:7]=[C:6]([CH3:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[C:10]1[C:11]([CH3:16])=[N:12][NH:13][C:14]=1[NH2:15].[C:18]([C:20](=[C:26](OCC)[CH3:27])[C:21]([O:23][CH2:24][CH3:25])=[O:22])#[N:19]>CO>[NH2:19][C:18]1[N:13]2[N:12]=[C:11]([CH3:16])[C:10]([C:3]3[C:4]([CH3:9])=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[CH3:17])=[C:14]2[N:15]=[C:26]([CH3:27])[C:20]=1[C:21]([O:23][CH2:24][CH3:25])=[O:22]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 46635Ethyl 2-cyano-3-ethoxy-2-butenoateHCID 178424562HCID 178424562, Verbindung

Produkt 1

HCID 22249773Ethyl 7-amino-mesityl-2,5-dimethylpyrazolo[1,5-a]pyrimidin-6-carboxylateAusbeute 20,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

Concentrated hydrochloric acid (0.1 mL) was added to a solution of 4-mesityl-3-methyl-1H-5-pyrazoleamine (2.5 g, 11.61 mmol) and ethyl 2-cyano-3-ethoxy-2-butenoate (2.13 g, 11.61 mmol) in methanol (30 mL), followed by heating under reflux for 18 hours. The reaction mixture was evaporated as it was. Then, water was added and a 5N aqueous solution of sodium hydroxide was added under ice-cooling, to neutralize. Further, the mixture was extracted with ethyl acetate, and the organic layer was washed with brine, dried over anhydrous magnesium sulfate and evaporated. The residue was purified by silica gel column chromatography (15% ethyl acetate/hexane), to give the title compound (835 mg).

Aufarbeitung

  1. temperatureby heating
  2. temperatureunder reflux for 18 hours
  3. customThe reaction mixture was evaporated as it
  4. additionThen, water was added
  5. additiona 5N aqueous solution of sodium hydroxide was added under ice-
  6. temperaturecooling
  7. extractionFurther, the mixture was extracted with ethyl acetate
  8. washthe organic layer was washed with brine
  9. dry with materialdried over anhydrous magnesium sulfate
  10. customevaporated
  11. customThe residue was purified by silica gel column chromatography (15% ethyl acetate/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-af8f0395d22b46a497e7bff9652ebe72
Quelldatensatz
uspto-grants-2005_10
Patentnummer
US06951865B2

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