Methyl iodide → 3-(3-bromo-2-methylphenyl)-7-fluoro-1-methylquinazoline-2,4(1H,3H)-dione

HRID 523227Notes

Reaction equation

HRID 523227 reaction equation
[Br:1][C:2]1[C:3]([CH3:21])=[C:4]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([F:19])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:20])[CH:5]=[CH:6][CH:7]=1.IC.[C:24]([O-])([O-])=O.[Cs+].[Cs+]>C1COCC1>[Br:1][C:2]1[C:3]([CH3:21])=[C:4]([N:8]2[C:17](=[O:18])[C:16]3[C:11](=[CH:12][C:13]([F:19])=[CH:14][CH:15]=3)[N:10]([CH3:24])[C:9]2=[O:20])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 1177609783-(3-bromo-2-methylphenyl)-7-fluoroquinazoline-2,4(1H,3H)-dione

Product 1

HCID 1177612893-(3-bromo-2-methylphenyl)-7-fluoro-1-methylquinazoline-2,4(1H,3H)-dioneYield 101.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-(3-bromo-2-methylphenyl)-7-fluoroquinazoline-2,4(1H,3H)-dione (2.70 g, 7.73 mmol), iodomethane (0.580 mL, 9.28 mmol) and Cs2CO3 (3.78 g, 11.6 mmol) in THF (20 mL) was stirred at room temperature for 3 h. The mixture was filtered and the filtrate was diluted with DCM and washed with water. The aqueous phase was extracted with DCM, and the combined organic phases were dried and concentrated to give 3-(3-bromo-2-methylphenyl)-7-fluoro-1-methylquinazoline-2,4(1H,3H)-dione (2.85 g), used without further purification. Mass spectrum m/z 363, 365 (M+H)+, 385, 387 (M+Na)+.

Workup

  1. filtrationThe mixture was filtered
  2. additionthe filtrate was diluted with DCM
  3. washwashed with water
  4. extractionThe aqueous phase was extracted with DCM
  5. customthe combined organic phases were dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d5f9ffa633654b5a8660c6b09a98b2d4
Source dataset
uspto-grants-2016_05
Patent number
US09334290B2

Reaction notes

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