Potassium Permanganate → (R)-2-(2-methoxyphenyl)-3-(1-phenylpropan-2-yl)-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1170917Notes

Reaction equation

HRID 1170917 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH:9]1[NH:14][C:13]2[CH:15]=[CH:16][N:17]=[C:18]([C:19]([F:22])([F:21])[F:20])[C:12]=2[C:11](=[O:23])[N:10]1[C@H:24]([CH3:32])[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.[Mn]([O-])(=O)(=O)=O.[K+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:10]([C@H:24]([CH3:32])[CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:11](=[O:23])[C:12]2[C:18]([C:19]([F:22])([F:21])[F:20])=[N:17][CH:16]=[CH:15][C:13]=2[N:14]=1

Participants

4

Reactant 2

HCID 516875Potassium PermanganateHCID 595538812-(2-methoxyphenyl)-3-((R)-1-phenylpropan-2-yl)-5-(trifluoromethyl)-2,3-dihydropyrido[4,3-d]pyrimidin-4(1H)-one

Product 1

HCID 59553889(R)-2-(2-methoxyphenyl)-3-(1-phenylpropan-2-yl)-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-(2-methoxyphenyl)-3-((R)-1-phenylpropan-2-yl)-5-(trifluoromethyl)-2,3-dihydropyrido[4,3-d]pyrimidin-4(1H)-one (19.04 g, 43.13 mmol) was dissolved in acetone (800 mL). To this was added a 5% aqueous solution of potassium permanganate (34.1 g KMnO4 in 700 mL water). The resultant mixture was stirred at room temperature overnight. The reaction was quenched by pouring it into a 10% aqueous solution of sodium bisulfite (3 L). The resulting aqueous solution was extracted with ethyl acetate (3×700 mL). The organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo to provide an oil. This oil was purified by flash chromatography using 25-50% ethyl acetate/heptanes as eluant to provide the product as a solid. This solid was recrystallized from ethyl acetate/hexanes to yield a colorless solid (12.5 g). 1H NMR (400 MHz, CDCl3) δ 8.8 (d, 1H), 7.65 (d, 1H), 7.4 (t, 1H), 7.15 (m, 7H), 6.95 (t, 1H), 6.8 (d, 1H), 6.35 (d, 1H), 4.2 (m, 1H), 3.8 (s, 3H), 3.6 (dd, 1H), 2.9 (dd, 1H), 1.75 (d, 3H). MS m/z 440.3 (M+H)+.

Workup

  1. customThe reaction was quenched
  2. additionby pouring it into a 10% aqueous solution of sodium bisulfite (3 L)
  3. extractionThe resulting aqueous solution was extracted with ethyl acetate (3×700 mL)
  4. washThe organic phase was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto provide an oil
  9. customThis oil was purified by flash chromatography

Sources & evidence

ORD record
ord-b62956811d4d4edbbe5bed4067783198
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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