Methyl iodide → HCID 117760705, compound

HRID 523210Notes

Reaction equation

HRID 523210 reaction equation
[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1.[C:21]([O-])([O-])=O.[Cs+].[Cs+].IC>CN(C=O)C>[Br:1][C:2]1[C:3]([CH3:20])=[C:4]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[N:10]([CH3:21])[C:9]2=[O:19])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 117760882HCID 117760882, compound

Product 1

HCID 117760705HCID 117760705, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 3-(3-bromo-2-methylphenyl)quinazoline-2,4(1H,3H)-dione (23.02 g, 69.5 mmol) and Cs2CO3 (34.0 g, 104 mmol) in DMF (70 mL) cooled in an ice-water bath was treated portionwise with iodomethane (5.22 mL, 83 mmol). The mixture was warmed to room temperature and stirred for 30 min. The mixture was filtered and the filtrate was concentrated. The residue was partitioned between EtOAc and water. A precipitate which formed was collected by filtration. The collected solid was washed with water and dried overnight under vacuum to give a white solid. The organic phase of the filtrate was separated, washed 3 times with 10% aqueous LiCl, then was washed twice with water, dried and concentrated to give additional solid. The two solids were combined to give 3-(3-bromo-2-methylphenyl)-1-methylquinazoline-2,4(1H,3H)-dione as a white solid (15.56 g, 92% yield). Mass spectrum m/z 345, 347 (M+H)+.

Workup

  1. temperaturecooled in an ice-water bath
  2. filtrationThe mixture was filtered
  3. concentrationthe filtrate was concentrated
  4. customThe residue was partitioned between EtOAc and water
  5. customA precipitate which formed
  6. filtrationwas collected by filtration
  7. washThe collected solid was washed with water
  8. customdried overnight under vacuum
  9. customto give a white solid
  10. customThe organic phase of the filtrate was separated
  11. washwashed 3 times with 10% aqueous LiCl
  12. washwas washed twice with water
  13. customdried
  14. concentrationconcentrated
  15. customto give additional solid

Sources & evidence

ORD record
ord-d96b34cf1bb64c24b30c5e3d89cf8f88
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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