Methyl iodide → 1-{4-[(4-chlorobenzyl)oxy]benzyl}-4-[4-(4-fluorophenyl)piperazin-yl]-6-methoxy-1,3,5-triazin-2(1H)-one

HRID 1477698Notes

Reaction equation

HRID 1477698 reaction equation
[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][O:7][C:8]2[CH:35]=[CH:34][C:11]([CH2:12][N:13]3[C:18](=[O:19])[N:17]=[C:16]([N:20]4[CH2:25][CH2:24][N:23]([C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)[CH2:22][CH2:21]4)[NH:15][C:14]3=[O:33])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[C:38](=O)([O-])[O-].[K+].[K+].CI>CN(C)C=O>[Cl:1][C:2]1[CH:37]=[CH:36][C:5]([CH2:6][O:7][C:8]2[CH:35]=[CH:34][C:11]([CH2:12][N:13]3[C:14]([O:33][CH3:38])=[N:15][C:16]([N:20]4[CH2:21][CH2:22][N:23]([C:26]5[CH:31]=[CH:30][C:29]([F:32])=[CH:28][CH:27]=5)[CH2:24][CH2:25]4)=[N:17][C:18]3=[O:19])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 1178398293-{4-[(4-Chlorobenzyl)oxy]benzyl}-6-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazine-2,4(1H,3H)-dione

Product 1

HCID 1178397731-{4-[(4-chlorobenzyl)oxy]benzyl}-4-[4-(4-fluorophenyl)piperazin-yl]-6-methoxy-1,3,5-triazin-2(1H)-oneYield 7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an N,N-dimethylformamide solution (4 mL) of a crude product (0.69 mmol) of 3-{4-[(4-chlorobenzyl)oxy]benzyl}-6-[4-(4-fluorophenyl)piperazin-1-yl]-1,3,5-triazine-2,4(1H,3H)-dione, potassium carbonate (332 mg, 2.40 mmol) and methyl iodide (137 μL, 2.20 mmol) were added at room temperature and the resultant mixture was stirred at room temperature for 1 day. After the completion of the reaction, the reaction solution was concentrated under reduced pressure and the resultant residue was purified by silica gel column chromatography to obtain the title compound (26 mg, two step yield: 7%).

Workup

  1. customAfter the completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. customthe resultant residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-5698fc973458407b8bcccda1bfa7cbbc
Source dataset
uspto-grants-2016_08
Patent number
US09403798B2

Reaction notes

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