Water → (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one

HRID 539129Notes

Reaction equation

HRID 539129 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C@H:7]1[CH2:11][O:10][C:9](=[O:12])[NH:8]1.[H-].[Na+].[Br:15][C:16]1[CH:17]=[N:18][N:19]2[CH:24]=[CH:23][C:22](Cl)=[N:21][C:20]=12.O>CN(C=O)C>[Br:15][C:16]1[CH:17]=[N:18][N:19]2[CH:24]=[CH:23][C:22]([N:8]3[C@@H:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[CH2:11][O:10][C:9]3=[O:12])=[N:21][C:20]=12

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10964848(S)-4-(pyridin-2-yl)oxazolidin-2-oneHCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 67034603(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-oneYield 57.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (S)-4-(pyridin-2-yl)oxazolidin-2-one (0.20 g, 1.2 mmol) in DMF (20 mL) was added sodium hydride (0.049 g, 1.2 mmol) and the reaction was stirred at ambient temperature for 1 hour. 3-Bromo-5-chloropyrazolo[1,5-a]pyrimidine (0.28 g, 1.2 mmol) was added and the reaction stirred for an additional 1 hour. The reaction was then poured into water (100 mL) and extracted into ether (200 mL). The organic layer was washed with water (100 mL), dried over MgSO4 and concentrated in vacuo. The crude material was chromatographed using 100% DCM to 15% EtOAc/DCM as eluent to yield (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-(pyridin-2-yl)oxazolidin-2-one (0.25 g, 56.8%).

Workup

  1. stirringthe reaction stirred for an additional 1 hour
  2. extractionextracted into ether (200 mL)
  3. washThe organic layer was washed with water (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude material was chromatographed

Sources & evidence

ORD record
ord-02f8ea9a110940d1a01388bd546f33de
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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