Sodium periodate → HCID 54765062, compound

HRID 2038191Notes

Reaction equation

HRID 2038191 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:13]([CH:14]([OH:18])[CH2:15][CH:16]=C)=[C:12]([CH:19]([CH3:21])[CH3:20])[N:11]=[C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:25])=[O:24])[N:9]=2)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:29].[Na+]>CO.[Os](=O)(=O)(=O)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:13]([CH:14]([OH:18])[CH2:15][CH:16]=[O:29])=[C:12]([CH:19]([CH3:20])[CH3:21])[N:11]=[C:10]([N:22]([CH3:27])[S:23]([CH3:26])(=[O:24])=[O:25])[N:9]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 54765061HCID 54765061, compound

Product 1

HCID 54765062HCID 54765062, compoundYield 3%

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[4-(4-fluorophenyl)-5-(1-hydroxybut-3-enyl)-6-isopropyl-pyrimidin-2-yl]-N-methylmethanesulfonamide (2 g, 5.08 mmol) in a mixture of 30 mL methanol and 4 mL buffer solution (pH=7), sodium periodate (3.2 g, 15.2 mmol) and osmium tetroxide (0.3 mL, 4% wt. in water, 13 mg) are added at room temperature. The reaction mass is stirred and the progress of the reaction is monitored by TLC. Upon completion of the reaction, the reaction mixture is filtered through celite bed (1 g) and washed with ethyl acetate (2×10 mL). The filtrate is distilled under reduced pressure until solvents are removed. To the residue, ethyl acetate (200 mL) is added and washed with DM water (50 mL) and brine (50 mL), subsequently. The solvent is distilled off under reduced pressure to afford 2.1 g crude product. Part of the residue (200 mg) is purified through silica gel column chromatography eluting with (20%-30%) ethylacetate:cyclohexane to obtain 60 mg pure N-(4-(4-fluorophenyl)-5-(1-hydroxy-3-oxopropyl)-6-isopropylpyrimidin-2-yl)-N-methylmethanesulfonamide.

Workup

  1. additionare added at room temperature
  2. customUpon completion of the reaction
  3. filtrationthe reaction mixture is filtered through celite bed (1 g)
  4. washwashed with ethyl acetate (2×10 mL)
  5. distillationThe filtrate is distilled under reduced pressure until solvents
  6. customare removed
  7. additionTo the residue, ethyl acetate (200 mL) is added
  8. washwashed with DM water (50 mL) and brine (50 mL)
  9. distillationThe solvent is distilled off under reduced pressure
  10. customto afford 2.1 g crude product
  11. customPart of the residue (200 mg) is purified through silica gel column chromatography
  12. washeluting with (20%-30%) ethylacetate

Sources & evidence

ORD record
ord-d0002cea4d7342f8b160ab9726452b63
Source dataset
uspto-grants-2013_11
Patent number
US08575343B2

Reaction notes

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