Potassium Permanganate → HCID 57636042, compound

HRID 216191Notes

Reaction equation

HRID 216191 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([CH:14]=[O:15])=[CH:11][CH:10]=2)[CH:6]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[N:4]=1.[Mn]([O-])(=O)(=O)=[O:28].[K+]>CC(C)=O.O>[CH3:1][O:2][C:3]1[N:8]=[C:7]([C:9]2[S:13][C:12]([C:14]([OH:28])=[O:15])=[CH:11][CH:10]=2)[CH:6]=[C:5]([NH:16][CH2:17][CH2:18][C:19]2[CH:20]=[CH:21][C:22]([O:25][CH3:26])=[CH:23][CH:24]=2)[N:4]=1

Participants

5

Reactant 2

HCID 516875Potassium PermanganateHCID 11501553HCID 11501553, compound

Product 1

HCID 57636042HCID 57636042, compoundYield 50%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

To a solution of 5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-thiophene-2-carbaldehyde [700 mg, 1.895 mmol, Example 8(b)] in acetone (20 mL) is added a solution of potassium permanganate (898 mg, 5.684 mmol) and NaH2PO4.H2O (79 mg, 0.568 mmol) in water (20 mL) followed by the addition of silica gel (4 g). The mixture is allowed to stir at ambient temperature for 6 hours, allowed to stand overnight, evaporated to remove the acetone and extracted several times with ethyl acetate. The organic extracts are combined and dried over magnesium sulfate, filtered and concentrated. The residual crude product is dissolved in refluxing acetonitrile and the solids that formed upon cooling are collected by filtration to afford 5-{2-methoxy-6-[2-(4-methoxy-phenyl)-ethylamino]-pyrimidin-4-yl}-thiophene-2-carboxylic acid [362 mg, 50%, Example 61].

Workup

  1. additionfollowed by the addition of silica gel (4 g)
  2. waitto stand overnight
  3. customevaporated
  4. customto remove the acetone
  5. extractionextracted several times with ethyl acetate
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe residual crude product is dissolved
  10. temperaturein refluxing acetonitrile
  11. customthe solids that formed
  12. temperatureupon cooling
  13. filtrationare collected by filtration

Sources & evidence

ORD record
ord-450129a18fee4adea94b22afbdaaa1f8
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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