Potassium Carbonate → HCID 89122965, compound

HRID 334324Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:8]=[C:7](/[CH:9]=[CH:10]\[C:11]2[CH:16]=[C:15]([O:17][CH3:18])[C:14]([O:19][CH3:20])=[C:13]([O:21][CH3:22])[CH:12]=2)[CH:6]=[C:5]([O:23][CH3:24])[C:4]=1[OH:25].C(=O)([O-])[O-].[K+].[K+].Br[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]2[NH:54][C:53](=[O:55])[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[NH:46]2)=[CH:41][C:40]=1[O:56][CH3:57]>CN(C=O)C.C(OCC)(=O)C.CCCCCC>[CH3:24][O:23][C:5]1[CH:6]=[C:7](/[CH:9]=[CH:10]\[C:11]2[CH:12]=[C:13]([O:21][CH3:22])[C:14]([O:19][CH3:20])=[C:15]([O:17][CH3:18])[CH:16]=2)[CH:8]=[C:3]([O:2][CH3:1])[C:4]=1[O:25][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][O:38][C:39]1[CH:44]=[CH:43][C:42]([CH:45]2[NH:54][C:53](=[O:55])[C:52]3[C:47](=[CH:48][CH:49]=[CH:50][CH:51]=3)[NH:46]2)=[CH:41][C:40]=1[O:56][CH3:57]

Participants

Conditions

Temperature: 30 °C

Procedure

(Z)-2,6-dimethoxy-4-(3,4,5-trimethoxystyryl)phenol (38b) (346.37.36 mg 1.0 mmol) in DMF (20 mL) was added anhydrous potassium carbonate (690 mg, 5.0 mmol) and 2-[4-(5-Bromo-pentyloxy)-3-methoxy-phenyl]-2,3-dihydro-1H-quinazolin-4-one (2d) (419.29 mg, 1.0 mmol). The reaction mixture was stirred at a temperature of 30° C. for 30 h and the reaction was monitored by TLC using ethyl acetate-hexane (6:4) as a solvent system. Then to this ice is added and extracted with ethyl acetate. The solvent was evaporated under vacuum to afford the crude product. This was further purified by column chromatography using ethyl acetate:hexane (6:4) as a solvent system to obtain the pure product (43d) (546 mg, 80% yield).

Workup

extractionextracted with ethyl acetate
customThe solvent was evaporated under vacuum
customto afford the crude product
customThis was further purified by column chromatography

Sources & evidence

ORD record: ord-5776ffa6485344caa1472f4906addbda
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08883809B2

Reaction notes

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