Potassium Carbonate → 1-[2-hydroxy-2-(2,4,6-trimethyl-phenyl)-ethyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

HRID 1046396

Reaction equation

HRID 1046396 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:19]3[C:14](=[CH:15][CH:16]=[C:17]([O:20][CH2:21][C:22]#[CH:23])[CH:18]=3)[NH:13][C:12](=[O:24])[N:11]=2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:25]1([CH3:36])[CH:30]=[C:29]([CH3:31])[CH:28]=[C:27]([CH3:32])[C:26]=1[CH:33]1[CH2:35][O:34]1.C(=O)([O-])[O-].[K+].[K+]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.O1CCOCC1>[OH:34][CH:33]([C:26]1[C:27]([CH3:32])=[CH:28][C:29]([CH3:31])=[CH:30][C:25]=1[CH3:36])[CH2:35][N:13]1[C:14]2[C:19](=[CH:18][C:17]([O:20][CH2:21][C:22]#[CH:23])=[CH:16][CH:15]=2)[C:10]([C:7]2[CH:6]=[CH:5][C:4]([CH:1]([CH3:3])[CH3:2])=[CH:9][CH:8]=2)=[N:11][C:12]1=[O:24]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 128628782-(2,4,6-Trimethylphenyl)oxiraneHCID 592591374-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Product 1

HCID 592591561-[2-hydroxy-2-(2,4,6-trimethyl-phenyl)-ethyl]-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 0.5 g (1.57 mmol) 4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one, 0.254 g (1.57 mmol) mesityl oxirane, 35.7 mg (0.157 mmol) benzyltriethylammonium chloride and 21.7 mg (0.157 mmol) potassium carbonate is stirred in 1 ml dioxane at 90° C. for 6 days. The reaction mixture is extracted with water/dichloromethane and, after evaporation of the organic phases, the residue is purified by preparative reversed phase HPLC.

Workup

  1. extractionThe reaction mixture is extracted with water/dichloromethane
  2. customafter evaporation of the organic phases
  3. customthe residue is purified by preparative reversed phase HPLC

Sources & evidence

ORD record
ord-3ceb0578e44b440aae5758693b6c2558
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Linked notes

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