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

HRID 1275875

Reaction equation

HRID 1275875 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 5-bromo-2,4-dichloropyrimidine (55 g) (J. Am. Chem. Soc. 1934, 56, 134) in tetrahydrofuran (100 ml) dropwise. After 1.5 hours, water (100 ml) was added carefully and the mixture extracted with ethyl acetate. The combined organic solution was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 5% triethylamine in isohexane to give the product as a solid. Yield 52.4 g

Workup

  1. extractionthe mixture extracted with ethyl acetate
  2. washThe combined organic solution was washed with water
  3. dry with materialdried (MgSO4)
  4. customevaporated under reduced pressure
  5. customPurification
  6. washeluting with 5% triethylamine in isohexane

Sources & evidence

ORD record
ord-976ad2b4a1e644e5a95fa7b91b4f4051
Source dataset
uspto-grants-2000_12
Patent number
US06162808

Linked notes

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