Water → 4-(2-Tetrahydropyranyloxy-2-(4-tert-butylphenyl)ethoxy)quinazoline

HRID 1392888Notes

Reaction equation

HRID 1392888 reaction equation
[OH:1][CH2:2][CH:3]([O:14][CH:15]1[CH2:20][CH2:19][CH2:18][CH2:17][O:16]1)[C:4]1[CH:9]=[CH:8][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:6][CH:5]=1.[H-].[Na+].Cl[C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[CH:26][N:25]=1.O>O1CCCC1>[O:16]1[CH2:17][CH2:18][CH2:19][CH2:20][CH:15]1[O:14][CH:3]([C:4]1[CH:5]=[CH:6][C:7]([C:10]([CH3:13])([CH3:12])[CH3:11])=[CH:8][CH:9]=1)[CH2:2][O:1][C:24]1[C:33]2[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=2)[N:27]=[CH:26][N:25]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 596787081-Hydroxy-2-tetrahydropyranyloxy-2-(4-tert-butylphenyl)ethane

Product 1

HCID 596786914-(2-Tetrahydropyranyloxy-2-(4-tert-butylphenyl)ethoxy)quinazoline

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1-Hydroxy-2-tetrahydropyranyloxy-2-(4-tert-butylphenyl) ethane (0.3 g, 1.07 mmol) is dissolved in dry tetrahydrofuran (7 ml) and to it is added sodium hydride (30.96 mg, 1.29 mmol). The resulting solution is stirred at room temperature for 30 minutes after which 4-chloroquinazoline (0.175 g, 1.07 mmol) is added to the above solution. The solution is then stirred for 6 hours after which water is added to the mixture. The solution is then extracted in dichloromethane. The organic layer is washed, dried and then concentrated to yield the crude product which is purified by flash chromatography (silica gel; ethyl acetate/hexanes) to give the product.

Workup

  1. additionis added to the above solution
  2. additionis added to the mixture
  3. extractionThe solution is then extracted in dichloromethane
  4. washThe organic layer is washed
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-5b82d2920b204bdba2568044ec0441d1
Source dataset
uspto-grants-2008_03
Patent number
US07344702B2

Reaction notes

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