Lithium Hydroxide → 3-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-ol

HRID 219704Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 219704
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20]C(=O)C)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 69025431Acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propyl ester

Produkt 1

HCID 690262333-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-olAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

7 g of acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propyl ester (18.7 mmol) and 0.67 g of lithium hydroxide (28.0 mmol) were stirred overnight in a mixture of 40 ml of tetrahydrofuran and 40 ml of water. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (2%) as eluent to yield 2.5 g of the title compound as an oil that crystallized upon standing.

Aufarbeitung

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe crude product was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-0965dbf844454989ae6335d53734cf5e
Quelldatensatz
uspto-grants-2012_06
Patentnummer
US08202868B2

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