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Dichloromethane → 2-Ethyl-5,7-dimethyl-3-[4-(piperidin-4-ylmethoxy)-benzyl]-pyrazolo[1,5-a]pyrimidine hydrochloride

HRID 403514
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 403514
[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2].C([N:29]1[CH2:34][CH2:33][CH:32]([CH2:35]O)[CH2:31][CH2:30]1)(OC(C)(C)C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C.[Cl:70]CCl>C(OC(=O)C)C>[ClH:70].[CH2:1]([C:3]1[C:13]([CH2:14][C:15]2[CH:16]=[CH:17][C:18]([O:21][CH2:35][CH:32]3[CH2:33][CH2:34][NH:29][CH2:30][CH2:31]3)=[CH:19][CH:20]=2)=[C:6]2[N:7]=[C:8]([CH3:12])[CH:9]=[C:10]([CH3:11])[N:5]2[N:4]=1)[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 6344DichloromethaneHCID 11776TriphenylphosphineHCID 2764081Tert-butyl 4-(hydroxymethyl)piperidine-1-carboxylateHCID 5363146Diisopropyl azodicarboxylateHCID 683792244-((2-Ethyl-5,7-dimethylpyrazolo[1,5-a]pyrimidin-3-yl)methyl)phenol

Produkt 1

HCID 68379288
2-Ethyl-5,7-dimethyl-3-[4-(piperidin-4-ylmethoxy)-benzyl]-pyrazolo[1,5-a]pyrimidine hydrochloride

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

4-(2-Ethyl-5,7-dimethyl-pyrazolo[1,5-a]pyrimidin-3-ylmethyl)-phenol (8), (0.12 g, 0.4 mmol) N-Boc-4-piperidinmethanol (0.11 g, 0.49 mmol) were dissolved in 3 ml of dichloromethane and triphenylphosphine (0.13 g, 0.49 mmol) and DIAD (0.12 g, 0.49 mmol) were added. The reaction mixture was stirred at rt for 12 h. It was then diluted with ethylacetate and the organic layer was washed with 5% aqueous NaHCO3 solution. The organic layer was washed again with brine and dried over Na2 SO4. It was then concentrated under reduced pressure and the crude product purified by chromatography to give the title compound as a white solid. Boc deprotection was performed analogously to example 3 step B.

Aufarbeitung

  1. washthe organic layer was washed with 5% aqueous NaHCO3 solution
  2. washThe organic layer was washed again with brine
  3. customdried over Na2 SO4
  4. concentrationIt was then concentrated under reduced pressure
  5. customthe crude product purified by chromatography

Quellen und Nachweise

ORD-Eintrag
ord-67eaf6fdd17f4eb7bd31175dc18f5e7b
Quelldatensatz
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08748435B2

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