Sodium hydride → HCID 22632943, compound

HRID 2270250Notes

Reaction equation

HRID 2270250 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+].[F:25][CH2:26][CH2:27]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]([CH2:27][CH2:26][F: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 24758Sodium hydrideHCID 69804Ethane, 1-fluoro-2-iodo-HCID 15908875HCID 15908875, compound

Product 1

HCID 22632943HCID 22632943, compoundYield 65.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
50 °C

Procedure

A solution of 3-benzyloxy-6,7-difluoro-1H-quinazoline-2,4-dione (Example B, 1.0 g, 3.2 mmol) in 20 mL of DMF was added to a suspension of sodium hydride (0.16 g, 3.9 mmol) in 20 mL of DMF and stirred for 30 minutes. 2-Fluoroethyl iodide (1.1 g, 6.4 mmol) was added, and the mixture was warmed to 50° 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 0.73 g of the title compound as a solid, mp 145-147° C.

Workup

  1. customThe reaction was quenched with 1 mL of water
  2. concentrationconcentrated to an oil
  3. dissolutionThe residue was dissolved in chloroform
  4. washwashed with water, brine
  5. dry with materialdried over magnesium sulfate
  6. concentrationThe solution was concentrated

Sources & evidence

ORD record
ord-6a3750ad5fb24326a3935abde6c2bb00
Source dataset
uspto-grants-2001_12
Patent number
US06331538B1

Reaction notes

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