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

HRID 1516105Notes

Reaction equation

HRID 1516105 reaction equation
C1(C)C=CC(S(OCCCC[CH:15]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[CH2:16][O:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=2)(=O)=O)=CC=1.[F-:35].[K+].C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[CH2:63]1[CH2:67]O[CH2:65][CH2:64]1>O>[F:35][CH2:65][CH2:64][CH2:63][CH2:67][C:31]1[CH:30]=[CH:29][C:28]([CH2:15][CH2:16][O:17][C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=2)=[CH:33][CH:32]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 23693052Potassium fluoride kryptofix 222HCID 1317298464-(4-p-Toluenesulfonyloxybutylphenyl 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-toluenesulfonyloxybutylphenyl 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-3de8dbeccae94205be82cfe38380e760
Source dataset
uspto-grants-2012_07
Patent number
US08226929B2

Reaction notes

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