Potassium Carbonate → 2-(6-quinazolinoxy)-N-(4-methylpent-2-yn-4-yl) butyramide

HRID 2222292Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][N:6]=[CH:5]2.Br[CH:13]([CH2:23][CH3:24])[C:14]([NH:16][C:17]([CH3:22])([CH3:21])[C:18]#[C:19][CH3:20])=[O:15].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C.CCCCCC>CN(C)C=O.O>[N:8]1[C:9]2[C:4](=[CH:3][C:2]([O:1][CH:13]([CH2:23][CH3:24])[C:14]([NH:16][C:17]([CH3:22])([CH3:21])[C:18]#[C:19][CH3:20])=[O:15])=[CH:11][CH:10]=2)[CH:5]=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

6-Hydroxyquinazoline (0.060 g, prepared as described in J. Chem. Soc. (1952), 4985) and 2-bromo-N-(4-methylpent-2-yn-4-yl) butyramide (0.101 g) were dissolved in dry N,N-dimethylformamide (2 ml) containing anhydrous potassium carbonate (0.088 g). The mixture was stirred and heated to 80° C. for 5 hours then allowed to cool to ambient temperature and stored for 18 hours. The brown suspension was diluted with water, extracted into ethyl acetate and the organic phase separated, washed with water, dried over magnesium sulphate and evaporated under reduced pressure to give a pale brown oil. The oil was fractionated by chromatography (silica; ethyl acetate/hexane, 4:1 by volume) to give the title product (0.12 g) as a pale brown gum.

Workup

temperatureto cool to ambient temperature
extractionextracted into ethyl acetate
customthe organic phase separated
washwashed with water
dry with materialdried over magnesium sulphate
customevaporated under reduced pressure
customto give a pale brown oil

Sources & evidence

ORD record: ord-9888df05067e419ca09645291a551921
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371764B2

Reaction notes

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