HCID 59553890, compound → 3-(1-(3,4-difluorophenyl)propan-2-yl)-2-(3-hydroxypyridin-2-yl)-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

HRID 1170914Notes

Reaction equation

HRID 1170914 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([N:12]2[C:17](=[O:18])[C:16]3[C:19]([C:23]([F:26])([F:25])[F:24])=[N:20][CH:21]=[CH:22][C:15]=3[NH:14][CH:13]2[C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]>CC(C)CC(=O)C.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][CH:10]([N:12]2[C:17](=[O:18])[C:16]3[C:19]([C:23]([F:24])([F:25])[F:26])=[N:20][CH:21]=[CH:22][C:15]=3[N:14]=[C:13]2[C:27]2[C:32]([OH:33])=[CH:31][CH:30]=[CH:29][N:28]=2)[CH3:11])[CH:5]=[CH:6][C:7]=1[F:8]

Participants

4

Reactant 1

HCID 59553890HCID 59553890, compound

Product 1

HCID 1359488083-(1-(3,4-difluorophenyl)propan-2-yl)-2-(3-hydroxypyridin-2-yl)-5-(trifluoromethyl)pyrido[4,3-d]pyrimidin-4(3H)-one

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 7909Methyl Isobutyl KetoneSolvent

Conditions

Temperature
90 °C

Procedure

3-(1-(3,4-difluorophenyl)propan-2-yl)-2-(3-hydroxypyridin-2-yl)-5-(trifluoromethyl)-2,3-dihydropyrido[4,3-d]pyrimidin-4(1H)-one (27.3 g, 58.8 mmol) was dissolved in 4-methyl-2-pentanone (500 mL). To this was added manganese dioxide (76.7 g, 882 mmol) and the mixture was heated to 90° C. for 1 hour. The reaction mixture was cooled and filtered through celite. The filter cake was washed with ethyl acetate. Combined filtrates were concentrated in vacuo to a pale yellow solid (8.35 g). The solid was slurried in hexanes and the resultant colorless solid was collected. The filtrate was concentrated and purified by silica gel column chromatography using 20-30% acetone/hexanes as eluant to yield additional product (3.47 g, 43.5% total yield).

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered through celite
  3. washThe filter cake was washed with ethyl acetate
  4. concentrationCombined filtrates were concentrated in vacuo to a pale yellow solid (8.35 g)
  5. customthe resultant colorless solid was collected
  6. concentrationThe filtrate was concentrated
  7. custompurified by silica gel column chromatography
  8. customto yield additional
  9. customproduct (3.47 g, 43.5% total yield)

Sources & evidence

ORD record
ord-e52daf9dfeb94ce48e04da2289a7490e
Source dataset
uspto-grants-2010_11
Patent number
US07829572B2

Reaction notes

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