HCID 69960504, compound → HCID 18918864, compound

HRID 1291403Notes

Reaction equation

HRID 1291403 reaction equation
[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:33])[C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)=[CH:18][CH:17]=1>C1COCC1.C(OCC)(=O)C.CO.[Pd]>[CH3:1][N:2]1[C:11](=[O:12])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[CH3:13])[N:4]=[C:3]1[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([C:22](=[O:33])[C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=2)=[CH:18][CH:17]=1

Participants

4

Reactant 1

HCID 69960504HCID 69960504, compound

Product 1

HCID 18918864HCID 18918864, compoundYield 34.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 19895526THF ethyl acetate methanolSolvent

Procedure

To a solution of 3,5-dimethyl-2-[2-[4-(4-trifluoromethylbenzoyl)phenyl]vinyl]-4(3H)-quinazolinone (897 mg) in THF: ethyl acetate: methanol (1:1:1) (60 ml) was added 10% Pd/C (50% hydrous) (179 mg) and the mixture was stirred under hydrogen at room temperature for 2 hours. The catalyst was then filtered off and the filtrate was concentrated. The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate =2:1) and recrystallized from ethyl acetate-methanol to provide 307 mg of white powder.

Workup

  1. filtrationThe catalyst was then filtered off
  2. concentrationthe filtrate was concentrated
  3. customThe residue was purified by silica gel column chromatography (n-hexane: ethyl acetate =2:1)
  4. customrecrystallized from ethyl acetate-methanol

Sources & evidence

ORD record
ord-a9464e878ab64bb09434c7b17c1439e1
Source dataset
uspto-grants-1998_05
Patent number
US05753664

Reaction notes

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