Dimethyl Sulfoxide → HCID 58149524, compound

HRID 714146Notes

Reaction equation

HRID 714146 reaction equation
CS(C)=O.[I-].[CH3:6][S+](C)(C)=O.[H-].[Na+].[CH3:13][C:14]([CH3:24])([CH3:23])[C:15]([C:17]1[CH:18]=[N:19][CH:20]=[N:21][CH:22]=1)=[O:16]>O1CCCC1>[C:14]([C:15]1([C:17]2[CH:22]=[N:21][CH:20]=[N:19][CH:18]=2)[CH2:6][O:16]1)([CH3:24])([CH3:23])[CH3:13]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 136456502,2-Dimethyl-1-(pyrimidin-5-yl)propan-1-one

Product 1

HCID 58149524HCID 58149524, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an atmosphere of argon, 10 ml of dimethyl sulphoxide are slowly added dropwise to 0.96 g (4.3 mmol) of trimethylsulphoxonium iodide and 0.17 g of sodium hydride (60%, 4.3 mmol). The reaction mixture is then stirred at room temperature for 15 min, and 0.65 g (3.9 mmol) of 2,2-dimethyl-1-(5-pyrimidinyl)-1-propanone, dissolved in 2 ml of tetrahydrofuran, is 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 with sodium sulphate, filtered and concentrated. This gives 0.70 g (99%) of the desired product, which is reacted without further purification.

Workup

  1. additionis 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 with sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThis gives 0.70 g (99%) of the desired product, which is reacted without further purification

Sources & evidence

ORD record
ord-781c71d9a53842b5a2eb37ac33e4a01f
Source dataset
uspto-grants-2015_11
Patent number
US09187431B2

Reaction notes

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