Methyl iodide → HCID 15390590, compound

HRID 1418293Notes

Reaction equation

HRID 1418293 reaction equation
[Cl:1][C:2]1[C:7]([OH:8])=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1.[C:21](=O)([O-])[O-].[K+].[K+].CI.[Cl-].[NH4+]>C(OCC)C.C(#N)C>[Cl:1][C:2]1[C:7]([O:8][CH3:21])=[CH:6][C:5]([N:9]2[C:17](=[O:18])[C:12]3=[CH:13][CH2:14][CH2:15][CH2:16][N:11]3[C:10]2=[O:19])=[C:4]([F:20])[CH:3]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 15390589HCID 15390589, compound

Product 1

HCID 15390590HCID 15390590, compoundYield 58.8%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6342AcetonitrileSolvent

Procedure

An acetonitrile (15 mL) solution of 2-(4-chloro-2-fluoro-5-hydroxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.78 g, 2.63 mmol), potassium carbonate (0.27 g, 1.97 mmol) and methyliodide (0.33 mL, 5.26 mmol) was stirred for 6.5 hours under reflux. A saturated ammonium chloride solution (15 mL) and diethyl ether (15 mL) were added to the resulting mixture, and the organic layer was separated and then the aqueous layer was extracted with diethyl ether (15 mL×2 times). The organic layer combined was washed with a saturated sodium chloride solution (20 mL) and dried over anhydrous magnesium sulfate. After removal of magnesium sulfate by filtration, the filtrate was evaporated to give crude product, which was purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/1) to obtain a white solid of 2-(4-chloro-2-fluoro-5-methyloxyphenyl)-5,6-dihydroimidazo [1,5-a] pyridine-1,3[2H, 7H]-dione (0.36 g, yield:44.3%).

Workup

  1. temperatureunder reflux
  2. customthe organic layer was separated
  3. extractionthe aqueous layer was extracted with diethyl ether (15 mL×2 times)
  4. washThe organic layer combined was washed with a saturated sodium chloride solution (20 mL)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter removal of magnesium sulfate
  7. filtrationby filtration
  8. customthe filtrate was evaporated
  9. customto give crude product, which
  10. customwas purified by silica gel column (Wakogel C-200, ethyl acetate/hexane=1/1)

Sources & evidence

ORD record
ord-8ed9495cdd5f43f1955995aaf38afa97
Source dataset
uspto-grants-1999_03
Patent number
US05883049

Reaction notes

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