Sodium hydride → HCID 54502880, compound

HRID 1956186Notes

Reaction equation

HRID 1956186 reaction equation
[CH3:1][NH:2][S:3]([CH3:6])(=[O:5])=[O:4].[CH3:7][C:8]1([CH3:27])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17]1[C:18](S(C)(=O)=O)=[N:19][CH:20]=[N:21][CH:22]=1.[H-].[Na+]>CN(C)C=O>[CH3:7][C:8]1([CH3:27])[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]1[C:17]1[C:18]([N:2]([S:3]([CH3:6])(=[O:5])=[O:4])[CH3:1])=[N:19][CH:20]=[N:21][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 97632N-MethylmethanesulfonamideHCID 23226984HCID 23226984, compound

Product 1

HCID 54502880HCID 54502880, compoundYield 10.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

N-Methylmethanesulfonamide (1.9 g) and then 1.2 g (17 mmol) of 5-(2,2-dimethylindan-1-yl)-4-methanesulfonylpyrimidine were added to a slurry of 0.40 g (17 mmol) of sodium hydride in 50 mL of dry N,N-dimethylformamide with stirring and the resulting mixture was heated at 80° C. for 1 hour. The mixture was then cooled and partitioned between ether and water. The organic phase was recovered, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure. The residue was purified by column chromatography on silica gel and 0.57 g of the title compound was obtained as a tan solid melting at 107°-109° C.

Workup

  1. temperatureThe mixture was then cooled
  2. custompartitioned between ether and water
  3. customThe organic phase was recovered
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated by evaporation under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-c6511361fb90466786df1e9f15333616
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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