Methyl iodide → HCID 22632983, compound

HRID 2270168Notes

Reaction equation

HRID 2270168 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+].[CH3:25]I>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]([CH3:25])[C:10]1=[O:22])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15908875HCID 15908875, compound

Product 1

HCID 22632983HCID 22632983, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-benzyloxy-6,7-difluoro-1H-quinazoline-2,4-dione (Example B, 1.5 g, 5 mmol) in 50 mL of DMF was added to a suspension of sodium hydride (0.24 g, 5.9 mmol) in 20 mL of DMF and stirred for 30 minutes. Methyl iodide (3.1 mL, 49 mmol) was added, and the mixture was stirred at 25° C. for 18 hours. The reaction was quenched with 1 mL 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 1.6 g of the title compound as a solid, mp 167-169° C.

Workup

  1. stirringthe mixture was stirred at 25° C. for 18 hours
  2. customThe reaction was quenched with 1 mL 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-2e83e04bde69450c9583cb7cb8c00dec
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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