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

HRID 1244811
Notes
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Reaction equation

HRID 1244811 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 589643Quinazolin-6-olHCID 210784062-bromo-N-(4-methylpent-2-yn-4-yl)butyramideHCID 21226206Ethyl acetate hexane

Product 1

HCID 692549702-(6-quinazolinoxy)-N-(4-methylpent-2-yn-4-yl) butyramideYield 93.9%

Reagents, catalysts & solvents 2

HCID 962
Water
Solvent
HCID 6228DimethylformamideSolvent

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

  1. temperatureto cool to ambient temperature
  2. extractionextracted into ethyl acetate
  3. customthe organic phase separated
  4. washwashed with water
  5. dry with materialdried over magnesium sulphate
  6. customevaporated under reduced pressure
  7. customto give a pale brown oil

Sources & evidence

ORD record
ord-0577450bb10c46ae8d4107c21ed17d1c
Source dataset
uspto-grants-2006_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07122672B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes