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Iodoethane → 3-Dibenzylamino-6,7-difluoro-1-ethyl-1H-quinazoline-2,4-dione

HRID 10315
Notes
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Reaction equation

HRID 10315 reaction equation
[CH2:1]([N:8]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[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+].[CH2:32](I)[CH3:33]>CN(C)C=O>[CH2:23]([N:8]([CH2:1][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)[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]([CH2:32][CH3:33])[C:10]1=[O:22])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 219790003-Dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione

Product 1

HCID 219794283-Dibenzylamino-6,7-difluoro-1-ethyl-1H-quinazoline-2,4-dioneYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 3-dibenzylamino-6,7-difluoro-1H-quinazoline-2,4-dione (Example 16) (0.43 g, 1.1 mmol) in 10 mL of N,N-dimethylformamide is added to a suspension of sodium hydride (0.05 g, 1.3 mmol) in 10 mL of N,N-dimethylformamide and stirred for 30 minutes. Ethyl iodide (0.13 mL, 1.6 mmol) is added, and the mixture is stirred at 25° C. for 18 hours. The reaction is quenched with 1 mL of water and concentrated in vacuo. The residue is dissolved in chloroform, washed with water, brine, and dried over magnesium sulfate. The solution is concentrated and purified via chromatography (SiO2, CHCl3) to give 0.34 g of the title compound as a solid, mp 133–135° C., MS CI, m/z 422 (MH+).

Workup

  1. stirringthe mixture is stirred at 25° C. for 18 hours
  2. customThe reaction is quenched with 1 mL of water
  3. concentrationconcentrated in vacuo
  4. dissolutionThe residue is dissolved in chloroform
  5. washwashed with water, brine
  6. dry with materialdried over magnesium sulfate
  7. concentrationThe solution is concentrated
  8. custompurified via chromatography (SiO2, CHCl3)

Sources & evidence

ORD record
ord-de33f49a4f9a4548b0cd9c65b986092f
Source dataset
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07094780B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes