Methyl iodide → HCID 117839479, compound

HRID 1477726Notes

Reaction equation

HRID 1477726 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:13]([OH:14])[CH2:12][N:11]([C:15]3[N:20]=[CH:19][N:18]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:10][CH:9]=2)=[CH:4][CH:3]=1.[CH2:32](N(CC)CC)C.CI.C(=O)([O-])[O-].[K+].[K+].[H-].[Na+]>O.ClCCl.CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]([O:14][CH3:32])[CH2:12][N:11]([C:15]3[N:20]=[CH:19][N:18]([CH2:21][C:22]4[S:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=4)[C:17](=[O:31])[N:16]=3)[CH2:10][CH:9]=2)=[CH:6][CH:7]=1

Participants

9

Reactant 5

HCID 6328Methyl iodide3×HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 24758Sodium hydrideHCID 78166221HCID 78166221, compound

Product 1

HCID 117839479HCID 117839479, compoundYield 15.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To an N,N-dimethylformamide (2.0 mL)-dichloromethane (2.0 mL) solution of 4-[4-(4-fluorophenyl)-5-hydroxy-5,6-dihydropyridin-1(2H)-yl]-1-{[5-(trifluoromethyl)thiophen-2-yl]methyl}-1,3,5-triazin-2(1H)-one (50.0 mg, 0.111 mmol) synthesized in Synthesis Example 190, triethylamine (23.2 μL, 0.167 mmol) and methyl iodide (20.6 μL, 0.332 mmol) were added at room temperature and the resultant mixture was stirred at room temperature for 1 day. Next, to the reaction solution, potassium carbonate (50.0 mg, 0.362 mmol) and methyl iodide (40.0 μL, 0.643 mmol) were added and the resultant mixture was stirred at 50° C. for 1 hour. Then, to the reaction solution, sodium hydride (12.0 mg, 0.500 mmol) and methyl iodide (40.0 μL, 0.643 mmol) were added and the resultant mixture was stirred at room temperature for 1 day. After the completion of the reaction, to the reaction solution, water was added and extraction with chloroform from the reaction solution was performed. The organic layer was dried over anhydrous magnesium sulfate and was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain the title compound (7.80 mg, yield: 15%).

Workup

  1. additionwere added at room temperature
  2. customAfter the completion of the reaction
  3. extractionextraction with chloroform from the reaction solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationwas concentrated under reduced pressure
  6. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-b7b5fbeef68243e3afd9bfd0d39519f6
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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