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

HRID 539064Notes

Reaction equation

HRID 539064 reaction equation
[Br:1][C:2]1[CH:3]=[N:4][N:5]2[CH:10]=[CH:9][C:8](Cl)=[N:7][C:6]=12.[CH2:12]([C@H:14]1[CH2:18][O:17][C:16](=[O:19])[NH:15]1)[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:15]3[C@@H:14]([CH2:12][CH3:13])[CH2:18][O:17][C:16]3=[O:19])=[N:7][C:6]=12

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 7832546(S)-4-ethyloxazolidin-2-oneHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 67033956(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-oneYield 56.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (0.375 g, 1.61 mmol) and (S)-4-ethyloxazolidin-2-one (0.279 g, 2.42 mmol) in DMF (10 mL) was added sodium hydride (0.0968 g, 2.42 mmol) at ambient temperature. The mixture was stirred for 18 hours. Saturated aqueous NH4Cl was added and the solids were collected by filtration. Purification of the crude material by column chromatography (1-10% EtOAc in DCM) provided (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-ethyloxazolidin-2-one (0.282 g, 56% yield) as a pale yellow solid.

Workup

  1. filtrationthe solids were collected by filtration
  2. customPurification of the crude material by column chromatography (1-10% EtOAc in DCM)

Sources & evidence

ORD record
ord-efb800951b63423b9528848313f9d9e4
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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