Sodium hydride → 4-(6-Ethoxytetralin-2-yloxy)quinazoline

HRID 1385891Notes

Reaction equation

HRID 1385891 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([OH:14])[CH2:8][CH2:7]2)[CH3:2].[H-].[Na+].Cl[C:18]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=[CH:20][N:19]=1>C1COCC1.CCOCC>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[CH2:10][CH:9]([O:14][C:18]1[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[N:21]=[CH:20][N:19]=1)[CH2:8][CH2:7]2)[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 788644-ChloroquinazolineHCID 118302726-Ethoxytetralin-2-ol

Product 1

HCID 110126414-(6-Ethoxytetralin-2-yloxy)quinazoline

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.57 g (13.3 mmol) of 6-ethoxytetralin-2-ol in 5 ml of THF were added, with ice-cooling, to a suspension of 400 mg of NaH (80% pure, 13.3 mmol in 40 ml of THF). The mixture was subsequently refluxed for 1 hour and cooled to room temperature, and 2.0 g (12.2 mmol) of 4-chloroquinazoline were added. The mixture was refluxed for 24 hours and cooled and then diluted with ether and washed with saturated sodium hydrogen carbonate and saturated sodium chloride solution. After the organic phase had been dried and concentrated, the residue was chromatographed on silica gel using petroleum ether/ethyl acetate (9:1, 8:2). This gave 2.39 g (61% of theory) of colorless crystals (m.p.115-117° C.).

Workup

  1. temperatureThe mixture was subsequently refluxed for 1 hour
  2. temperatureThe mixture was refluxed for 24 hours
  3. temperaturecooled
  4. washwashed with saturated sodium hydrogen carbonate and saturated sodium chloride solution
  5. customAfter the organic phase had been dried
  6. concentrationconcentrated
  7. customthe residue was chromatographed on silica gel

Sources & evidence

ORD record
ord-7b9e9785ddf64b9686c66a0c08697aac
Source dataset
uspto-grants-2001_07
Patent number
US06265398B1

Reaction notes

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