Ethyl Acetate → 2-Chloro-4-(1,1-dimethylethoxy)pyrimidine

HRID 606148Notes

Reaction equation

HRID 606148 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1.[CH3:9][C:10]([CH3:13])([O-:12])[CH3:11].[K+].C(OCC)(=O)C>C(O)(C)(C)C>[C:10]([O:12][C:2]1[N:7]=[C:6]([Cl:8])[CH:5]=[CH:4][N:3]=1)([CH3:13])([CH3:11])[CH3:9].[C:10]([O:12][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:13])([CH3:11])[CH3:9]

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 775312,4-DichloropyrimidineHCID 23665647Potassium tert-butoxide

Product 2

HCID 22248001HCID 22248001, compoundYield 16%HCID 222483182-Chloro-4-(1,1-dimethylethoxy)pyrimidineYield 50%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

After dissolving 2.00 g of 2,4-dichloropyrimidine in 30 ml of tert-butanol, 1.58 g of potassium tert-butoxide was added while stirring and the mixture was stirred overnight at room temperature. The reaction mixture was poured onto ice and extraction was performed with ethyl acetate. The organic layer was washed with water and saturated brine in that order and dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate), to obtain 2-tert-butoxy-4-chloropyrimidine (0.40 g, 16% yield) and 4-tert-butoxy-2-chloropyrimidine (1.28 g, 50% yield).

Workup

  1. additionwas added
  2. stirringthe mixture was stirred overnight at room temperature
  3. additionThe reaction mixture was poured onto ice and extraction
  4. washThe organic layer was washed with water and saturated brine in that order
  5. dry with materialdried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (solvent: n-hexane/ethyl acetate)

Sources & evidence

ORD record
ord-38242157317449b4ac11ff958ce18693
Source dataset
uspto-grants-2011_03
Patent number
US07915274B2

Reaction notes

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