Sodium hydride → 4-(5-Benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline

HRID 855672Notes

Reaction equation

HRID 855672 reaction equation
[CH2:1]([C:8]1[CH2:12][C:11](=[O:13])[NH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl[C:17]1[C:26]2[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]3[CH2:38][CH2:37][O:36][CH2:35][CH2:34]3)=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>CN(C=O)C.[Cl-].[NH4+]>[CH2:1]([C:8]1[NH:9][N:10]=[C:11]([O:13][C:17]2[C:26]3[C:21](=[CH:22][C:23]([O:29][CH2:30][CH2:31][CH2:32][N:33]4[CH2:34][CH2:35][O:36][CH2:37][CH2:38]4)=[C:24]([O:27][CH3:28])[CH:25]=3)[N:20]=[CH:19][N:18]=2)[CH:12]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 118239414-Chloro-6-methoxy-7-(3-morpholin-4-ylpropoxy)quinazolineHCID 220592713-benzyl-1H-pyrazol-5(4H)-one

Product 1

HCID 179427484-(5-Benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazolineYield 79%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Procedure

3-Benzyl-4,5-dihydro-1H-pyrazol-5-one (174 mg, 1 mmol), (J. Chem. Soc. Perk. Trans 1, 1980, 1618-1621), was added to a suspension of sodium hydride (40 mg, 1 mmol, prewashed with pentane) in DMF (3 ml) under nitrogen. After stirring for 30 minutes at ambient temperature, 4-chloro-6-methoxy-7-(3-morpholinopropoxy)quinazoline (135 mg, 0.4 mmol) was added and the mixture was heated at 80° C for 1 hour. After cooling, the mixture was diluted with saturated aqueous ammonium chloride solution and partitioned between ethyl acetate and water. The precipitate was collected by filtration, washed with water, followed by ethanol, ether and dried under vacuum to give 4-(5-benzylpyrazol-3-yloxy)-6-methoxy-7-(3-morpholinopropoxy)quinazoline (150 mg, 79%).

Workup

  1. temperaturethe mixture was heated at 80° C for 1 hour
  2. temperatureAfter cooling
  3. custompartitioned between ethyl acetate and water
  4. filtrationThe precipitate was collected by filtration
  5. washwashed with water
  6. customdried under vacuum

Sources & evidence

ORD record
ord-861d09854a0c4fa9811eae4b0e2e2452
Source dataset
uspto-grants-2007_08
Patent number
US07262201B1

Reaction notes

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