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Hydrochloric Acid → 6-(4-Benzylphenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 460695
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 460695
C([O:3][C:4]([C:6]1[CH:7]=[N:8][N:9]2[C:14]([CH:15]3[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]3)=[C:13]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][C:28]4[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=4)=[CH:23][CH:22]=3)[CH:12]=[N:11][C:10]=12)=[O:5])C.[Li+].[OH-].Cl>O1CCCC1>[CH2:27]([C:24]1[CH:25]=[CH:26][C:21]([C:13]2[CH:12]=[N:11][C:10]3[N:9]([N:8]=[CH:7][C:6]=3[C:4]([OH:5])=[O:3])[C:14]=2[CH:15]2[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]2)=[CH:22][CH:23]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 691557876-(4-Benzyl-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester

Produkt 1

HCID 159581186-(4-Benzylphenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acidAusbeute 21 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 36 mg (0.082 mmol) of 6-(4-benzyl-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid ethyl ester in 3 mL of tetrahydrofuran was added 0.5 mL (0.5 mmol) of 1 M LiOH solution, and the resulting mixture was heated at reflux overnight. The reaction mixture was then acidified with 1 M HCl solution to pH=2, and extracted with ethyl acetate. The combined organic extracts were dried over sodium sulfate, and concentrated to give a residue which was purified via reverse-phase chromatography to afford (after lyophilization) 7 mg (21% yield) of 6-(4-benzyl-phenyl)-7-cyclohexyl-pyrazolo[1,5-a]pyrimidine-3-carboxylic acid as a solid (90% purity, entry 444) as indicated by 1H NMR; LC-MS—calcd for C26H25N3O2 [M++H]+: 412.19, found: 412.3.

Aufarbeitung

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic extracts were dried over sodium sulfate
  5. concentrationconcentrated
  6. customto give a residue which
  7. customwas purified via reverse-phase chromatography

Quellen und Nachweise

ORD-Eintrag
ord-30d511ea27554c93b70fdf1bc02efbd0
Quelldatensatz
uspto-grants-2007_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07196111B2

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