Sodium hydride → HCID 23447336, compound

HRID 1840583Notes

Reaction equation

HRID 1840583 reaction equation
[I-].[CH3:2][S+](C)(C)=O.[H-].[Na+].[Cl:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([N:16]2[CH2:21][CH2:20][C:19](=[O:22])[CH2:18][CH2:17]2)[CH:11]=1>CS(C)=O>[Cl:9][C:10]1[N:15]=[CH:14][N:13]=[C:12]([N:16]2[CH2:17][CH2:18][C:19]3([O:22][CH2:2]3)[CH2:20][CH2:21]2)[CH:11]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 22000287HCID 22000287, compound

Product 1

HCID 23447336HCID 23447336, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of trimethylsulfoxonium iodide (10.56 g) in dimethylsulfoxide (50 ml) was added 60% sodium hydride (1.84 g) in oil, and the mixture was stirred at room temperature for 1 hour. To the mixture was added, under ice-cooling, 1-(6-chloropyrimidine-4-yl)piperidin-4-one (8.50 g), and the mixture was stirred at room temperature for 3 hours. The reaction solution was poured into ice-water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried and concentrated, and the residue was crystallized from diethylether to give colorless crystals of 6-(6-chloropyrimidine-4-yl)-1-oxa-6-azaspiro[2,5]octane (5.67 g).

Workup

  1. additionTo the mixture was added, under ice-
  2. temperaturecooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated brine
  5. customdried
  6. concentrationconcentrated
  7. customthe residue was crystallized from diethylether

Sources & evidence

ORD record
ord-8cc1cdc5d9a74859848fc406530a2005
Source dataset
uspto-grants-2004_01
Patent number
US06680312B2

Reaction notes

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