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

HRID 539060Notes

Reaction equation

HRID 539060 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:15]1[CH2:19][O:18][C:17](=[O:20])[NH:16]1)[CH2:13][CH3:14].[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]([CH2:12][CH2:13][CH3:14])[CH2:19][O:18][C:17]3=[O:20])=[N:7][C:6]=12

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 8063309AG-E-14754HCID 454805073-Bromo-5-chloropyrazolo(1,5-a)pyrimidine

Product 1

HCID 67034378(S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-oneYield 63%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-5-chloropyrazolo[1,5-a]pyrimidine (5.30 g, 22.8 mmol) and (S)-4-propyloxazolidin-2-one (0.354 g, 2.74 mmol) in dry DMF (10 mL) at ambient temperature was added sodium hydride (0.110 g, 2.74 mmol) and the solution was stirred for 18 hours. Saturated aqueous NH4Cl solution was added and the solids were collected by filtration. Purification of the crude material by normal phase column chromatography, eluting with 1-10% EtOAc/dichloromethane afforded 0.372 g (63%) of (S)-3-(3-bromopyrazolo[1,5-a]pyrimidin-5-yl)-4-propyloxazolidin-2-one as a yellow solid.

Workup

  1. filtrationthe solids were collected by filtration
  2. customPurification of the crude material by normal phase column chromatography
  3. washeluting with 1-10% EtOAc/dichloromethane

Sources & evidence

ORD record
ord-e0476fbd87bc4675ab7a577312b0771f
Source dataset
uspto-grants-2014_10
Patent number
US08865726B2

Reaction notes

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