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3-Pentanol → 7-(1-Ethyl-propoxy)-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

HRID 2183535
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2183535
[CH3:1][CH2:2][CH:3]([OH:6])[CH2:4][CH3:5].[H-].[Na+].Cl[C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]3[C:24]([CH3:25])=[CH:23][C:22]([CH3:26])=[CH:21][C:20]=3[CH3:27])=[C:14]2[N:13]=[C:12]([CH3:28])[CH:11]=1>C1COCC1>[CH2:2]([CH:3]([O:6][C:10]1[N:15]2[N:16]=[CH:17][C:18]([C:19]3[C:20]([CH3:27])=[CH:21][C:22]([CH3:26])=[CH:23][C:24]=3[CH3:25])=[C:14]2[N:13]=[C:12]([CH3:28])[CH:11]=1)[CH2:4][CH3:5])[CH3:1]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 114283-PentanolHCID 24758Sodium hydrideHCID 224743217-Chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 98842487-(1-Ethyl-propoxy)-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidineAusbeute 88 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

A solution of 3-pentanol (140 mg, 1.5 mmol) in 1 ml of dry THF was treated with 60% sodium hydride in oil (28 mg, 0.7 mmol) and stirred at room temperature for 10 min. A solution of 7-chloro-5-methyl-3-(2,4,6-trimethyl-phenyl)-pyrazolo[1,5-a]pyrimidine (75 mg, 0.262 mmol) in 1 ml of dry THF was added and the resulting mixture was heated at reflux for 5 hours. The mixture was quenched with water and extracted with ethyl acetate. The organic layer was washed with brine, dried and concentrated to give the crude material. The residue was purified through silica gel column chromatography using 3:7 chcloroform:hexane as eluent to give 75 mg (88%) of the title compound. 1H NMR (CDCl3) ä 7.97(s, 1H), 6.97(s, 2H), 6.03(s, 1H), 4.56(m, 1H), 2.53(s, 3H), 2.32(s, 3H), 2.13(s, 6H), 2.10(m, 4H), 1.09(t, 6H) ppm.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 5 hours
  3. customThe mixture was quenched with water
  4. extractionextracted with ethyl acetate
  5. washThe organic layer was washed with brine
  6. customdried
  7. concentrationconcentrated
  8. customto give the crude material
  9. customThe residue was purified through silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-867cc18c2d8a4bfab9f340db8e9a94eb
Quelldatensatz
uspto-grants-2005_05
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06900217B2

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