Dimethyl Sulfoxide → HCID 58149520, compound

HRID 593198Notes

Reaction equation

HRID 593198 reaction equation
CS(C)=O.[I-].[CH3:6][S+](C)(C)=O.[H-].[Na+].[CH3:13][CH:14]([CH3:23])[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[N:21][CH:22]=1)=[O:16]>O1CCCC1>[CH:14]([C:15]1([C:17]2[CH:22]=[N:21][CH:20]=[N:19][CH:18]=2)[CH2:6][O:16]1)([CH3:23])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 13645651HCID 13645651, compound

Product 1

HCID 58149520HCID 58149520, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon, 50 ml of dimethyl sulphoxide were slowly added dropwise to 8.06 g (37 mmol) of trimethylsulphoxonium iodide and 1.47 g of sodium hydride (60%, 37 mmol). The reaction mixture was then stirred at room temperature for 15 min, and 5.00 g (33 mmol) of 2-methyl-1-(5-pyrimidinyl)-1-propanone, dissolved in 10 ml of tetrahydrofuran, were added. The reaction mixture was stirred at 50° C. for 90 min. The reaction mixture was then concentrated under reduced pressure, and saturated aqueous sodium chloride solution and ethyl acetate were added to the residue. The organic phase was separated off, dried over sodium sulphate, filtered and concentrated. This gave 1.36 g (25%) of the desired product, which was reacted without further purification.

Workup

  1. additionwere added
  2. stirringThe reaction mixture was stirred at 50° C. for 90 min
  3. concentrationThe reaction mixture was then concentrated under reduced pressure, and saturated aqueous sodium chloride solution and ethyl acetate
  4. additionwere added to the residue
  5. customThe organic phase was separated off
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThis gave 1.36 g (25%) of the desired product, which was reacted without further purification

Sources & evidence

ORD record
ord-48b2c08e1b06420d9740be76a30e1b42
Source dataset
uspto-grants-2016_01
Patent number
US09241487B2

Reaction notes

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