Acetic Anhydride → Acetic acid 2-[4-(4-isopropyl-phenyl)-2-oxo-6-prop-2-ynyloxy-2H-quinazolin-1-yl]-1-phenyl-ethyl ester

HRID 445186Notes

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].[OH-].[Na+].[C:36](OC(=O)C)(=[O:38])[CH3:37]>>[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][CH:2]([O:1][C:36](=[O:38])[CH3:37])[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:5](=[O:27])[N:6]=2)=[CH:23][CH:22]=1)([CH3:26])[CH3:25]

Participants

Reactant 3

HCID 7918Acetic Anhydride

HCID 14798Sodium Hydroxide

HCID 601127781-(2-hydroxy-2-phenyl-ethyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one

Product 1

HCID 60112788Acetic acid 2-[4-(4-isopropyl-phenyl)-2-oxo-6-prop-2-ynyloxy-2H-quinazolin-1-yl]-1-phenyl-ethyl ester

Procedure

A solution of 100 mg (0.228 mmol) 1-(2-hydroxy-2-phenyl-ethyl)-4-(4-isopropyl-phenyl)-6-prop-2-ynyloxy-1H-quinazolin-2-one in 1 ml acetic anhydride is heated at 100° C. for 18 h. The reaction mixture is poured onto 1 M aqueous NaOH and extracted with ether. The product is purified by preparative reversed phase HPLC.

Workup

extractionextracted with ether
customThe product is purified by preparative reversed phase HPLC

Sources & evidence

ORD record: ord-476a91732545487ebaf4cae0190cb6e7
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08476286B2

Reaction notes

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