Water → HCID 23502535, compound

HRID 1597180Notes

Reaction equation

HRID 1597180 reaction equation
[NH2:1][C:2]1[C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=[C:4]([F:13])[C:3]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[NH:16][C:15]1=[O:25].[C:26](=O)([O-])[O-].[K+].[K+].IC.O>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[C:7]2[NH:8][C:9](=[O:12])[CH2:10][O:11][C:6]=2[CH:5]=[C:4]([F:13])[C:3]=1[N:14]1[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:26])[C:15]1=[O:25]

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 20688824HCID 20688824, compound

Product 1

HCID 23502535HCID 23502535, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-[5-Amino-7-fluoro-2H-1,4-benzoxazine-3(4H)-on-6-yl]-6-trifluoromethyl-2,4-(1H, 3H)-pyrimidinedione (4.0 g) was dissolved in DMF (200 ml) containing potassium carbonate (5 g) and iodomethane (10 ml). After stirring for 2 hr, water (150 ml) and ethyl acetate (200 ml) were added. The organic phase was washed with water (50 ml×3) and brine (50 ml), dried over sodium sulfate. After filtration and evaporation, the residue was recrystallized from methylene chloride and hexane to afford the title compound (3.3 g).

Workup

  1. washThe organic phase was washed with water (50 ml×3) and brine (50 ml)
  2. dry with materialdried over sodium sulfate
  3. filtrationAfter filtration and evaporation
  4. customthe residue was recrystallized from methylene chloride and hexane

Sources & evidence

ORD record
ord-233dfc0f885447c583885c0233dff61e
Source dataset
uspto-grants-2001_09
Patent number
US06294503B1

Reaction notes

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