Pyrazol-3-ylamine → HCID 178507945, Verbindung

HRID 869453Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 869453
C(=O)(O)[O-].[Na+].Cl.C(O[C:10](=[NH:17])[CH2:11][C:12](OCC)=[O:13])C.[NH:18]1[C:22]([NH2:23])=[CH:21][CH:20]=[N:19]1>C(OCC)(=O)C.C(O)C>[NH2:17][C:10]1[NH:23][C:22]2[N:18]([N:19]=[CH:20][CH:21]=2)[C:12](=[O:13])[CH:11]=1

Komponenten

6

Edukt 3

HCID 74561Pyrazol-3-ylamineHCID 75345Ethyl 3-ethoxy-3-iminopropionate hydrochlorideHCID 516892Sodium Bicarbonate

Produkt 1

HCID 178507945HCID 178507945, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Sodium bicarbonate (3.9 g, 46.2 mmol) is added in small portions to a mixture of ethyl 3-ethoxy-3-iminopropanoate hydrochloride (Z-1) (8.6 g, 44.0 mmol) in crushed ice (100 g) and ethyl acetate (50 mL) until the pH value reaches 8-9. The organic layer is separated and the aqueous layer was extracted with ethyl acetate (2×50 mL). The combined organic layers are dried over anhydrous MgSO4 and filtered. The filtrate is concentrated in vacuo to afford a colourless oil which is added to a solution of 1H-pyrazol-5-amine (3.65 g, 44.0 mmol) in ethanol (100 mL). The resulting mixture is then degassed and backfilled with argon (three cycles) and stirred at reflux overnight. The mixture is then filtered while it was still warm. The solid is rinsed with cold ethanol (25 mL) and ether (2×25 mL), and then dried in vacuo to afford 5-aminopyrazolo[1,5-a]pyrimidin-7(4H)-one (Z-2).

Aufarbeitung

  1. customThe organic layer is separated
  2. extractionthe aqueous layer was extracted with ethyl acetate (2×50 mL)
  3. dry with materialThe combined organic layers are dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate is concentrated in vacuo
  6. customto afford a colourless oil which
  7. customThe resulting mixture is then degassed
  8. temperatureat reflux overnight
  9. filtrationThe mixture is then filtered while it
  10. temperaturewas still warm
  11. washThe solid is rinsed with cold ethanol (25 mL) and ether (2×25 mL)
  12. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-83a3ef8817454955a2bd21b5a21c158a
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08969363B2

Notizen zur Reaktion

Wird geladen…