Dimethyl Sulfoxide → HCID 58149520, compound

HRID 2170406Notes

Reaction equation

HRID 2170406 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 are 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 is 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, are added. The reaction mixture is stirred at 50° C. for 90 min. The reaction mixture is then concentrated under reduced pressure, and saturated aqueous sodium chloride solution and ethyl acetate are added to the residue. The organic phase is separated off, dried over sodium sulphate, filtered and concentrated. This gives 1.36 g (25%) of the desired product, which is reacted without further purification.

Workup

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

Sources & evidence

ORD record
ord-9f5b4f4f9dee415b88995181ecd02c12
Source dataset
uspto-grants-2015_06
Patent number
US09051277B2

Reaction notes

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