Water → 5-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine

HRID 1871962Notes

Reaction equation

HRID 1871962 reaction equation
[CH3:1][C:2]([CH3:5])([O-:4])[CH3:3].[K+].[Br:7][C:8]1[C:9](Cl)=[N:10][C:11](Cl)=[N:12][CH:13]=1.[OH2:16]>O1CCCC1>[Br:7][C:8]1[C:9]([O:16][C:2]([CH3:5])([CH3:3])[CH3:1])=[N:10][C:11]([O:4][C:2]([CH3:5])([CH3:3])[CH3:1])=[N:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2899735-Bromo-2,4-dichloropyrimidineHCID 23665647Potassium tert-butoxide

Product 1

HCID 8188515-Bromo-2,4-bis(1,1-dimethylethoxy)pyrimidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of potassium tert-butoxide (67.5 g) in tetrahydrofuran (500 ml) was added dropwise a solution of 5-bromo-2,4-dichloropyrimidine (55 g) (J.Am.Chem.Soc. 1934,56,134) in tetrahydrofuran (100 ml). After 1.5 hours, water (100 ml) was added carefully and the mixture extracted with ethyl acetate. The combined extract was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 5% triethylamine in isohexane. Yield 52.4 g.

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with water
  4. dry with materialdried (MgSO4)
  5. customevaporated under reduced pressure
  6. customPurification
  7. washeluting with 5% triethylamine in isohexane

Sources & evidence

ORD record
ord-2fee19ad102b4c10baaa6ff64a6bc187
Source dataset
uspto-grants-2000_08
Patent number
US06107297

Reaction notes

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