Sodium hydride → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one

HRID 538976Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 538976
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8](Cl)=[N:7][C:6]=12.[CH:12]([C@H:15]1[CH2:19][O:18][C:17](=[O:20])[NH:16]1)([CH3:14])[CH3:13].[H-].[Na+].[NH4+].[Cl-]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8]([N:16]3[C@@H:15]([CH:12]([CH3:14])[CH3:13])[CH2:19][O:18][C:17]3=[O:20])=[N:7][C:6]=12

Komponenten

6

Edukt 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7157133(4S)-4-(propan-2-yl)-1,3-oxazolidin-2-oneHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

Produkt 1

HCID 67034128(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-oneAusbeute 71,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (5.30 g, 22.8 mmol) and (S)-4-isopropyloxazolidin-2-one (4.42 g, 34.2 mmol) in dry DMF (100 mL) at ambient temperature was added sodium hydride (0.821 g, 34.2 mmol) and the solution stirred for 12 hours. Saturated aqueous NH4Cl solution was added and the solids were collected by filtration. Purification of the crude material by column chromatography, eluting with 1% MeOH/dichloromethane afforded 5.30 g (71%) of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-isopropyloxazolidin-2-one as a yellow solid. LCMS (APCI+) m/z 325, 327 [M+H]+.

Aufarbeitung

  1. filtrationthe solids were collected by filtration
  2. customPurification of the crude material by column chromatography
  3. washeluting with 1% MeOH/dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-fc58a014df7c4ca99455b3a6880dd7a9
Quelldatensatz
uspto-grants-2014_10
Patentnummer
US08865726B2

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