Sodium Thiosulfate → 4-[4-(2-Fluoro-phenyl)-2-oxo-2H-pyrimidin-1-yl]-butyraldehyde

HRID 1514435Notes

Reaction equation

HRID 1514435 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][CH2:16][CH2:17][OH:18])[C:10](=[O:19])[N:9]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][N:11]([CH2:14][CH2:15][CH2:16][CH:17]=[O:18])[C:10](=[O:19])[N:9]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 592427824-(2-Fluoro-phenyl)-1-(4-hydroxy-butyl)-1H-pyrimidin-2-one

Product 1

HCID 592428054-[4-(2-Fluoro-phenyl)-2-oxo-2H-pyrimidin-1-yl]-butyraldehydeYield 64%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(2-fluoro-phenyl)-1-(4-hydroxy-butyl)-1H-pyrimidin-2-one (80 mg, 0.30 mmol) in DCM (8 ml), the solution at 0° C., solid Dess Martin periodinane (380 mg, 0.61 mmol) was added portionwise. The mixture was stirred at room temperature for 1 hour. Na2S2O3 was added and the mixture was extracted with DCM; the organic layer was dried (Na2SO4), filtered and evaporated. The crude was purified by flash chromatography with ethyl acetate to give 50 mg of the title compound as a green solid (64% yield).

Workup

  1. extractionthe mixture was extracted with DCM
  2. dry with materialthe organic layer was dried (Na2SO4)
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude was purified by flash chromatography with ethyl acetate

Sources & evidence

ORD record
ord-1764c00be0d14417a08799e08551746d
Source dataset
uspto-grants-2012_07
Patent number
US08222266B2

Reaction notes

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