Sodium hydride → HCID 22633030, compound

HRID 2270256Notes

Reaction equation

HRID 2270256 reaction equation
[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:21])=[C:15]([F:20])[CH:16]=2)[NH:11][C:10]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:26][CH:27]1[CH2:29][CH2:28]1>CN(C=O)C>[CH2:1]([O:8][N:9]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][C:14]([F:21])=[C:15]([F:20])[CH:16]=2)[N:11]([CH2:26][CH:27]2[CH2:29][CH2:28]2)[C:10]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 81503BromomethylcyclopropaneHCID 15908875HCID 15908875, compound

Product 1

HCID 22633030HCID 22633030, compoundYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-benzyloxy-6,7-difluoro-1H-quinazoline-2,4-dione (Example B, 1.22 g, 4 mmol) in 25 mL of DMF was added to a suspension of sodium hydride (0.19 g, 4.8 mmol) in 20 mL of DMF and stirred for 30 minutes. Bromomethylcyclopropane (0.6 mL, 6.0 mmol) was added, and the mixture was stirred at 25° C. for 18 hours. The reaction was quenched with 1mL of water and concentrated to an oil. The residue was dissolved in chloroform, washed with water, brine, and dried over magnesium sulfate. The solution was concentrated to give 1.10 g of the title compound as a solid, mp 121-123° C.

Workup

  1. stirringthe mixture was stirred at 25° C. for 18 hours
  2. customThe reaction was quenched with 1mL of water
  3. concentrationconcentrated to an oil
  4. dissolutionThe residue was dissolved in chloroform
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-e1efbb9054624fe0b94e54757007a425
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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