Tetrahydrofuran → 4-(2-(4-(4-Fluorobutyl)phenyl)ethoxy)quinazoline

HRID 1751882Notes

Reaction equation

HRID 1751882 reaction equation
C1(C)C=CC(S(O[CH2:11][CH2:12][CH2:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][O:23][C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[N:27]=[CH:26][N:25]=3)=[CH:17][CH:16]=2)(=O)=O)=CC=1.[F-:35].[K+].C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.C1COCC1>O>[F:35][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][CH2:22][O:23][C:24]2[C:33]3[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=3)[N:27]=[CH:26][N:25]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23693052Potassium fluoride kryptofix 222HCID 596786134-(2-(4-(4-p-Toluenesulfonyloxybutyl)phenyl)ethoxy) quinazoline

Product 1

HCID 596786454-(2-(4-(4-Fluorobutyl)phenyl)ethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

4-(2-(4-(4-p-toluenesulfonyloxybutyl)phenyl)ethoxy) quinazoline (0.3 g, 0.63 mmol) is added to a solution of potassium fluoride/kryptofix 222 in 5 ml THF (1:1 ratio, 3.15 mmol each). After stirring at room temperature for 15 minutes the solution is then refluxed for 20 minutes. It is then cooled and water is added to it. The solution is then extracted in dichloromethane and washed with water and dried. The crude product is purified by silica gel flash chromatography (ethyl acetate/hexanes) to afford the product.

Workup

  1. temperatureis then refluxed for 20 minutes
  2. temperatureIt is then cooled
  3. extractionThe solution is then extracted in dichloromethane
  4. washwashed with water
  5. customdried
  6. customThe crude product is purified by silica gel flash chromatography (ethyl acetate/hexanes)
  7. customto afford the product

Sources & evidence

ORD record
ord-ac75e13dbe3f4d15a631f2b2adc46fd9
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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