Sodium hydride → HCID 22129650, compound

HRID 1857363Notes

Reaction equation

HRID 1857363 reaction equation
[H-].[Na+].[Br:3][C:4]1[C:9]([OH:10])=[N:8][C:7]([S:11][CH3:12])=[CH:6][N:5]=1.Br[CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16]>C1COCC1>[Br:3][C:4]1[C:9](=[O:10])[N:8]([CH2:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:7]([S:11][CH3:12])=[CH:6][N:5]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 178503308HCID 178503308, compound

Product 1

HCID 22129650HCID 22129650, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

SODIUM HYDRIDE (40 MG OF A 60% DISPERSION IN MINERAL OILS, 1.0 MMOL) WAS ADDED TO A STIRRED SOLUTION OF 2-BROMO-3-HYDROXY-5-METHYLTHIOPYRAZINE (100 MG, 0.45 MMOL) IN DRY THF (10 ML) UNDER ARGON. T-BUTYL BROMOACTATE (202 MICROL, 1.5 MMOL) WAS ADDED AND THE REACTION WAS STIRRED FOR 16 H. THE VOLATILES WERE EVAPORATED IN VACUO AND THE RESIDUE WAS PARTITIONED BETWEEN WATER AND METHYLENE CHLORIDE. THE ORGANIC LAYER WAS DRIED (NA2SO4) AND EVAPORATED IN VACUO. THE CRUDE PRODUCT WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (30% ETHYL ACETATE/HEXANES) TO GIVE THE TITLE COMPOUND AS A CRYSTALLINE SOLID:

Workup

  1. customTHE VOLATILES WERE EVAPORATED IN VACUO
  2. customTHE RESIDUE WAS PARTITIONED BETWEEN WATER AND METHYLENE CHLORIDE
  3. customTHE ORGANIC LAYER WAS DRIED (NA2SO4)
  4. customEVAPORATED IN VACUO
  5. customTHE CRUDE PRODUCT WAS PURIFIED BY FLASH COLUMN CHROMATOGRAPHY ON SILICA GEL (30% ETHYL ACETATE/HEXANES)

Sources & evidence

ORD record
ord-4cc76c0007bb4232b47d9db6c8e123d7
Source dataset
uspto-grants-2000_11
Patent number
US06147078

Reaction notes

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