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Triethylamine → [6-(3-Hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amine

HRID 1452623
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1452623
[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6](Cl)[N:5]2[N:13]=[CH:14][CH:15]=[C:4]2[N:3]=1.C(N(CC)CC)C.[CH3:23][CH2:24][O:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[CH:28][CH:27]=1>C(O)(C)C>[Cl:1][C:2]1[C:7]([CH2:8][CH2:9][CH2:10][OH:11])=[C:6]([NH:32][C:29]2[CH:30]=[CH:31][C:26]([O:25][CH2:24][CH3:23])=[CH:27][CH:28]=2)[N:5]2[N:13]=[CH:14][CH:15]=[C:4]2[N:3]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 90764-EthoxyanilineHCID 575268493-(5,7-Dichloropyrazolo[1,5-a]pyrimidin-6-yl)propan-1-ol

Produkt 1

HCID 57526854[6-(3-Hydroxypropyl)-5-chloropyrazolo[1,5-a]pyrimidin-7-yl](4-ethoxyphenyl)amineAusbeute 67,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To an isopropanol (3 mL) solution containing 3-(5,7-dichloropyrazolo[1,5-a]pyrimidin-6-yl)propan-1-ol (224 mg, 0.910 mmol), triethylamine (253 μL, 1.82 mmol) and phenethidine (128 μL, 1.00 mmol) were added, and this mixture was stirred at 40° C. for 5 hr. After the reaction, the solvent was distilled off, aqueous sodium hydrogen carbonate was added to the residue, and the mixture was extracted with ethyl acetate. The combined ethyl acetate layer was dried over sodium sulfate. After the sodium sulfate was filtered off, the filtrate was concentrated and the residue was purified with column chromatography (30% ethyl acetate-hexane) to obtain the title compound (212 mg).

Aufarbeitung

  1. additionwere added
  2. customAfter the reaction
  3. distillationthe solvent was distilled off
  4. additionaqueous sodium hydrogen carbonate was added to the residue
  5. extractionthe mixture was extracted with ethyl acetate
  6. dry with materialThe combined ethyl acetate layer was dried over sodium sulfate
  7. filtrationAfter the sodium sulfate was filtered off
  8. concentrationthe filtrate was concentrated
  9. customthe residue was purified with column chromatography (30% ethyl acetate-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c62276d5338a481cb80cd81436d76fe6
Quelldatensatz
uspto-grants-2009_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07473694B2

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