Imidazole → HCID 135996327, compound

HRID 2255099Notes

Reaction equation

HRID 2255099 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].[H][H].Br[CH2:11][C:12]1[CH:13]=[C:14]2[C:19](=[CH:20][CH:21]=1)[N:18]=[C:17]([CH2:22][CH2:23][CH3:24])[NH:16][C:15]2=[O:25]>CN(C=O)C.CCOC(C)=O>[N:1]1([CH2:11][C:12]2[CH:13]=[C:14]3[C:19](=[CH:20][CH:21]=2)[N:18]=[C:17]([CH2:22][CH2:23][CH3:24])[NH:16][C:15]3=[O:25])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

7

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 135676430HCID 135676430, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 135996327HCID 135996327, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of 0.20 g (3 mmol) of imidazole in 3 mL of dry DMF was added 79 mg of 80% NaH (3.3 mmol). After hydrogen evolution had ceased a solution of 0.28 g (1 mmol) of 6-bromomethyl-2-propylquinazolin-4(3H)-one was added in 1 mL of DMF. The reaction mixture was heated at 60° C. for 6 hours and was then stirred at room temperature for a further 2 days. The mixture was diluted with 25 mL of EtOAc and washed with saturated NaHCO3 (1×5 mL), water (1×5 mL) and brine (1×5 mL) and was dried over MgSO4. The solution was filtered and concentrated in vacuo and the residue was purified by flash chromatography over silica gel eluting with 7% MeOH/CH2Cl2 to provide the title compound.

Workup

  1. washwashed with saturated NaHCO3 (1×5 mL), water (1×5 mL) and brine (1×5 mL)
  2. dry with materialwas dried over MgSO4
  3. filtrationThe solution was filtered
  4. concentrationconcentrated in vacuo
  5. customthe residue was purified by flash chromatography over silica gel eluting with 7% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-0cf42220fc6a4fec8bd06e2bfb9cbaff
Source dataset
uspto-grants-1993_08
Patent number
US05238942

Reaction notes

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