Methyl iodide → HCID 21265564, compound

HRID 566193Notes

Reaction equation

HRID 566193 reaction equation
[CH2:1]([O:4][C:5]1[C:6]([Br:24])=[CH:7][C:8]([F:23])=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[NH:13][C:12]2=[O:22])[CH:10]=1)[CH:2]=[CH2:3].CI.[C:27](=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:1]([O:4][C:5]1[C:6]([Br:24])=[CH:7][C:8]([F:23])=[C:9]([N:11]2[C:16](=[O:17])[CH:15]=[C:14]([C:18]([F:21])([F:19])[F:20])[N:13]([CH3:27])[C:12]2=[O:22])[CH:10]=1)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21265592HCID 21265592, compound

Product 1

HCID 21265564HCID 21265564, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A crude product (16.67 g) of 3-(5-allyloxy-4-bromo-2-fluorophenyl)-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione, methyl iodide (7.18 g) and potassium carbonate (7.03 g) were suspended in DMF (80 ml), and the mixture was stirred at room temperature for 8 hours. After the reaction, DMF was distilled off under reduced pressure, extracted with ethyl acetate, washed with water, and dried over anhydrous magnesium sulfate. Then, ethyl acetate was distilled off, and the resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3 v/v), and the resulting oily substance was crystallized from ethyl acetate-n-hexane to obtain the objective 3-(5-allyloxy-4-bromo-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (5.42 g).

Workup

  1. distillationwas distilled off under reduced pressure
  2. extractionextracted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationThen, ethyl acetate was distilled off
  6. customthe resulting oily substance was purified by chromatography on silica gel (ethyl acetate:n-hexane=1:3 v/v)
  7. customthe resulting oily substance was crystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-52db300dc7544dbba4c59224ac2f33d5
Source dataset
uspto-grants-2001_01
Patent number
US06174839B1

Reaction notes

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