Potassium Carbonate → HCID 15839199, compound

HRID 2119434Notes

Reaction equation

HRID 2119434 reaction equation
[OH:1][CH:2]([C:5]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:6][CH3:7])[C:3]#[N:4].C(=O)([O-])[O-].[K+].[K+].CS([C:30]1[N:35]=[C:34]([O:36][CH3:37])[CH:33]=[C:32]([O:38][CH3:39])[N:31]=1)(=O)=O>CN(C=O)C>[CH3:39][O:38][C:32]1[CH:33]=[C:34]([O:36][CH3:37])[N:35]=[C:30]([O:1][CH:2]([C:5]([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[CH2:6][CH3:7])[C:3]#[N:4])[N:31]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 23442232HCID 23442232, compound

Product 1

HCID 15839199HCID 15839199, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.0 g (27.9 mmol) of 2-hydroxy-3,3-diphenylvaleronitrile were dissolved in 100 ml of DMF (abs.) and, under nitrogen, 7.57 g (55.7 mmol) of potassium carbonate and 6.1 g (27.9 mmol) of 2-methanesulfonyl-4,6-dimethoxypyrimidine were added, and the mixture was stirred at room temperature for 72 hours. The mixture was concentrated under reduced pressure, and the residue was taken up in water and extracted three times with ethyl acetate. The combined organic phases were dried over MgSO4, and the solvent was evaporated off. The crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1). 8.8 g (81%) of product were obtained.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic phases were dried over MgSO4
  4. customthe solvent was evaporated off
  5. customThe crude product was chromatographed on silica gel with n-heptane/ethyl acetate (20:1)

Sources & evidence

ORD record
ord-8d77aac4bcde41a594604832698eba7e
Source dataset
uspto-grants-2004_02
Patent number
US06686369B1

Reaction notes

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