Potassium Permanganate → HCID 59553904, compound

HRID 1170920Notes

Reaction equation

HRID 1170920 reaction equation
[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[CH:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])[NH:7][C:6]=2[CH:5]=[CH:4][N:3]=1.[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[Cl:1][C:2]1[C:11]2[C:10](=[O:12])[N:9]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[C:8]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[O:27][CH3:28])=[N:7][C:6]=2[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 516875Potassium Permanganate2×HCID 59553893HCID 59553893, compound

Product 1

HCID 59553904HCID 59553904, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
20 °C

Procedure

5-Chloro-2-(2-methoxy-phenyl)-3-phenethyl-2,3-dihydro-1H-pyrido[4,3-d]pyrimidin-4-one (1.0 g, 2.54 mmol) was placed in a flask, acetone (10 mL) was added and the mixture stirred vigorously at 20° C. A 5% aqueous solution of potassium permanganate (KMnO4) was added (50.8 mmol, 2 equiv.). The reaction progress was monitored by HPLC. The reaction was stirred for 12 hours. Another 2 equiv. of KMnO4 was added and reaction stirred at ambient temperature for 4 hours until reaction was complete according to HPLC. The reaction was then quenched with 10% aqueous NaHSO3, filtered by gravity filtration and partitioned between ethyl acetate and water. The aqueous layer was extracted 3× with ethyl acetate, the combined organic layers washed 1× with water, 1× brine and then dried over anhydrous Na2SO4. Filtration and evaporation of the solvent gave 398 mg of tan solid. The original filter cake was suspended in dichloromethane and sonicated for 5 minutes, then repeated two more times. The suspensions were filtered through a nylon filter, combined and evaporated to dryness to give additional 282 mg of product for combined total crude yield of 680 mg (68%) of a tan solid. The product was used further without purification.

Workup

  1. stirringThe reaction was stirred for 12 hours
  2. customreaction
  3. stirringstirred at ambient temperature for 4 hours until reaction
  4. customThe reaction was then quenched with 10% aqueous NaHSO3
  5. filtrationfiltered by gravity filtration
  6. custompartitioned between ethyl acetate and water
  7. extractionThe aqueous layer was extracted 3× with ethyl acetate
  8. washthe combined organic layers washed 1× with water, 1× brine
  9. dry with materialdried over anhydrous Na2SO4
  10. filtrationFiltration and evaporation of the solvent

Sources & evidence

ORD record
ord-c11b032a65554b3ea83f08935bc37051
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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