Water → 6-Fluoro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline

HRID 1751887

Reaction equation

HRID 1751887 reaction equation
[F-:1].[K+].C1N2CCOCCOCCN(CCOCCOCC2)CCOCCOC1.[N+]([C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[CH:37][N:36]=[C:35]2[O:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:47][CH:46]=1)([O-])=O.O>C1COCC1>[F:1][C:32]1[CH:33]=[C:34]2[C:39](=[CH:40][CH:41]=1)[N:38]=[CH:37][N:36]=[C:35]2[O:42][CH2:43][CH2:44][C:45]1[CH:50]=[CH:49][C:48]([C:51]([CH3:54])([CH3:53])[CH3:52])=[CH:47][CH:46]=1

Participants

6

Reactant 4

HCID 962WaterHCID 728012,2,2-CryptandHCID 522689Potassium FluorideHCID 596786596-Nitro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline

Product 1

HCID 596786656-Fluoro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 25 ml round bottom flask is added potassium fluoride (82.6 mg, 1.42 mmol) and kryptofix 222 (0.53 g, 1.42 mmol). The above mixture is stirred in THF for 20 minutes after which 6-Nitro-4-(2-(4-tert-butylphenyl)ethoxy)quinazoline (0.1 g, 0.284 mmol) is added to it. The solution is refluxed for 30 minutes after which it is cooled and water is added to it. It is then extracted in dichloromethane, washed with water and dried. Purification by flash chromatography (silica gel; ethyl acetate/hexanes) gives the above compound.

Workup

  1. additionis added to it
  2. temperatureThe solution is refluxed for 30 minutes after which it
  3. temperatureis cooled
  4. extractionIt is then extracted in dichloromethane
  5. washwashed with water
  6. customdried
  7. customPurification by flash chromatography (silica gel; ethyl acetate/hexanes)
  8. customgives the above compound

Sources & evidence

ORD record
ord-280ed8f1df244515957cbfa95d39d1fd
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Linked notes

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