Dimethylformamide → 5-Bromo-2-(2,2-diethoxyethoxy)pyrimidine

HRID 15063

Reaction equation

HRID 15063 reaction equation
[CH2:1]([O:3][CH:4]([O:7][CH2:8][CH3:9])[CH2:5][OH:6])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C.[Br:21][C:22]1[CH:23]=[N:24][C:25](Cl)=[N:26][CH:27]=1>O>[Br:21][C:22]1[CH:23]=[N:24][C:25]([O:6][CH2:5][CH:4]([O:7][CH2:8][CH3:9])[O:3][CH2:1][CH3:2])=[N:26][CH:27]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 121292,2-DiethoxyethanolHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 684312375-Bromo-2-(2,2-diethoxyethoxy)pyrimidineYield 94.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2,2-Diethoxyethanol (1.6 g) and cesium carbonate (5.8 g) were added to DMF solution (10 mL) of 5-bromo-2-chloropyrimidine (1.15 g), and stirred at room temperature for 12 hours. After addition of water, the reaction liquid was extracted with ethyl acetate and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4) to provide the title compound (1.63 g, 94%).

Workup

  1. customthe reaction liquid
  2. extractionwas extracted with ethyl acetate
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationConcentrating the solvent under reduced pressure
  5. customthe residue was purified on silica gel column chromatography (C-200; ethyl acetate:hexane=1:9-1:4)

Sources & evidence

ORD record
ord-1ba2013ec1264fe3af9606dd2c8fb343
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Linked notes

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