Water → HCID 15337738, compound

HRID 1801625Notes

Reaction equation

HRID 1801625 reaction equation
[OH:1][CH:2]([C:5]([O:18][CH3:19])([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[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.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]([O:18][CH3:19])([C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:3]#[N:4])[N:31]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 21927795α-Hydroxy-β-methoxy-β-phenylbenzenepropanenitrile

Product 1

HCID 15337738HCID 15337738, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

7.3 g (28.8 mmol) of 2-hydroxy-3-methoxy-3,3-diphenylpropionitrile were dissolved in 90 ml of DMF, and 4 g (28.8 mmol) of K2CO3 and 6.3 g (28 mmol) of 2-methanesulfonyl-4,6-dimethoxypyrimidine were added. The mixture was stirred at room temperature for about 12 h, then poured into water and extracted with ethyl acetate. The combined organic phases were washed again with H2O, dried and concentrated. The residue obtained in this way was then purified by chromatography on silica gel (n-hepane/ethyl acetate).

Workup

  1. extractionextracted with ethyl acetate
  2. washThe combined organic phases were washed again with H2O
  3. customdried
  4. concentrationconcentrated
  5. customThe residue obtained in this way
  6. customwas then purified by chromatography on silica gel (n-hepane/ethyl acetate)

Sources & evidence

ORD record
ord-7a7a7a84708a4438a2d9c3b485afdf87
Source dataset
uspto-grants-2013_01
Patent number
US08349843B2

Reaction notes

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