Sodium hydride → 1-(4-Bromo-phenyl)-3-[3-(3-isopropoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-urea

HRID 1292076Notes

Reaction equation

HRID 1292076 reaction equation
[NH2:1][C:2]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:21])[CH3:20])[CH:13]=2)[C:10](=[O:22])[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[N:3]=1.[H-].[Na+].[Br:25][C:26]1[CH:31]=[CH:30][C:29]([N:32]=[C:33]=[O:34])=[CH:28][CH:27]=1>CN(C=O)C>[Br:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]([NH:1][C:2]2[N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH:19]([CH3:20])[CH3:21])[CH:13]=3)[C:10](=[O:22])[C:9]3[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:3]=2)=[O:34])=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 756094-Bromophenyl isocyanateHCID 108277054(3H)-Quinazolinone, 2-amino-3-[3-(1-methylethoxy)phenyl]-

Product 1

HCID 105771091-(4-Bromo-phenyl)-3-[3-(3-isopropoxy-phenyl)-4-oxo-3,4-dihydro-quinazolin-2-yl]-ureaYield 14.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-amino-3-(3-isopropoxy-phenyl)-3H-quinazolin-4-one (295 mg, 1.0 mmol) in anhydrous DMF (10 mL) was added 50% NaH (48 mg, 1 mmol) at room temperature and stirred for 30 minutes. To this mixture was added, 4-bromo phenyl isocyanate and stirred for 2 hours at room temperature. The reaction mixture was quenched with water and concentrated. It was then diluted with ethyl acetate and filtered. The filtrate was concentrated and chromatographed using 100% CH3Cl to isolate pure product as a white solid (70 mg, 14.2%), mp 230°-233° C.

Workup

  1. additionTo this mixture was added
  2. customThe reaction mixture was quenched with water
  3. concentrationconcentrated
  4. additionIt was then diluted with ethyl acetate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. customchromatographed

Sources & evidence

ORD record
ord-d3bb63bb5c1247668b5309bb785614b0
Source dataset
uspto-grants-1998_05
Patent number
US05756502

Reaction notes

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