Cesium carbonate → 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one

HRID 1846261Notes

Reaction equation

[CH:1]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=[C:12]2[C:22]2[CH:27]=[C:26]([CH3:28])[C:25]([OH:29])=[C:24]([CH3:30])[CH:23]=2)=[CH:7][CH:6]=1)([CH2:3][CH3:4])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:38][CH2:39][O:40][Si:41]([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42]>CN(C=O)C>[Si:41]([O:40][CH2:39][CH2:38][O:29][C:25]1[C:24]([CH3:30])=[CH:23][C:22]([C:12]2[N:11]([C:8]3[CH:7]=[CH:6][C:5]([CH:1]([CH2:3][CH3:4])[CH3:2])=[CH:10][CH:9]=3)[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]=2)=[CH:27][C:26]=1[CH3:28])([C:44]([CH3:47])([CH3:46])[CH3:45])([CH3:43])[CH3:42]

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of 3-(4-sec-butylphenyl)-2-(4-hydroxy-3,5-dimethylphenyl)quinazolin-4(3H)-one in anhydrous DMF were added cesium carbonate and (2-bromo-ethoxy)-tert-butyl-dimethyl-silane at room temperature. The reaction mixture was stirred at 80° C. under nitrogen for 15 hours. The reaction mixture was cooled to room temperature and compound 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-3,5-dimethylphenyl)-3-(4-sec-butylphenyl)quinazolin-4(3H)-one (G) was isolated and optionally purified.

Workup

temperatureThe reaction mixture was cooled to room temperature

Sources & evidence

ORD record: ord-a142bc208d8b4ad685239750194c66a2
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952021B2

Reaction notes

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