Methyl iodide → 3-(3-fluoro-4-(methyl(2-morpholinoethyl)amino)phenyl)-2,6-dimethylpyrimidin-4(3H)-one

HRID 56160Notes

Reaction equation

HRID 56160 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])[N:19]=[C:18]2[CH3:25])[CH:5]=[CH:6][C:7]=1[NH:8][CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.[C:26]([O-])([O-])=O.[K+].[K+].CI>C(#N)C>[F:1][C:2]1[CH:3]=[C:4]([N:17]2[C:22](=[O:23])[CH:21]=[C:20]([CH3:24])[N:19]=[C:18]2[CH3:25])[CH:5]=[CH:6][C:7]=1[N:8]([CH3:26])[CH2:9][CH2:10][N:11]1[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 729498333-(3-fluoro-4-((2-morpholinoethyl)amino)phenyl)-2,6-dimethyl pyrimidin-4(3H)-one

Product 1

HCID 729498343-(3-fluoro-4-(methyl(2-morpholinoethyl)amino)phenyl)-2,6-dimethylpyrimidin-4(3H)-oneYield 20.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 3-(3-fluoro-4-((2-morpholinoethyl)amino)phenyl)-2,6-dimethyl pyrimidin-4(3H)-one (0.24 g, 0.69 mmol) and K2CO3 (0.48 g, 3.47 mmol) in acetonitrile (15 mL) was added CH3I (0.30 g, 2.11 mmol). The mixture was stirred at rt for 36 h, then filtered and concentrated in vacuo. The residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=50:1) to give the title compound as a white solid (50 mg, 20%). The compound was characterized by the following spectroscopic data:

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by a silica gel column chromatography (EtOAc/MeOH (V/V)=50:1)

Sources & evidence

ORD record
ord-2a06e185b4c34fbcac5b9be6bfddfaae
Source dataset
uspto-grants-2016_09
Patent number
US09434695B2

Reaction notes

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