1-(2-hydroxy-2-phenyl-ethyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one → 4-(4-isopropyl-phenyl)-1-(2-oxo-2-phenyl-ethyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

HRID 445187Notes

Reaction equation

HRID 445187 reaction equation
[OH:1][CH:2]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)[CH2:3][N:4]1[C:13]2[C:8](=[CH:9][C:10]([O:14][CH2:15][C:16]#[CH:17])=[CH:11][CH:12]=2)[C:7]([C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH3:26])[CH3:25])=[CH:20][CH:19]=2)=[N:6][C:5]1=[O:27].CC(C)=O.OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[CH:24]([C:21]1[CH:20]=[CH:19][C:18]([C:7]2[C:8]3[C:13](=[CH:12][CH:11]=[C:10]([O:14][CH2:15][C:16]#[CH:17])[CH:9]=3)[N:4]([CH2:3][C:2](=[O:1])[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:5](=[O:27])[N:6]=2)=[CH:23][CH:22]=1)([CH3:26])[CH3:25]

Participants

4

Reactant 2

HCID 601127781-(2-hydroxy-2-phenyl-ethyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-oneHCID 131709961Jones' reagent

Product 1

HCID 601128774-(4-isopropyl-phenyl)-1-(2-oxo-2-phenyl-ethyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 200 mg (0.456 mmol) 1-(2-hydroxy-2-phenyl-ethyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one in 2 ml acetone are added 0.17 ml (0.45 mmol) Jones reagent. After stirring for 30 minutes at rt aqueous work up followed by recrystallisation from ethyl acetate yields 4-(4-isopropyl-phenyl)-1-(2-oxo-2-phenyl-ethyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one.

Workup

  1. customup followed by recrystallisation from ethyl acetate

Sources & evidence

ORD record
ord-1095e420b55141a5a71b6d23d0959cbf
Source dataset
uspto-grants-2013_07
Patent number
US08476286B2

Reaction notes

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