Methyl iodide → 4-{5-Acetyl-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-4-pyrimidinyl}benzonitrile

HRID 230286Notes

Reaction equation

HRID 230286 reaction equation
[C:1]([C:4]1[CH:5]([C:22]2[CH:29]=[CH:28][C:25]([C:26]#[N:27])=[CH:24][CH:23]=2)[NH:6][C:7](=[S:21])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2].IC.[C:32](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:4]1[CH:5]([C:22]2[CH:23]=[CH:24][C:25]([C:26]#[N:27])=[CH:28][CH:29]=2)[N:6]=[C:7]([S:21][CH3:32])[N:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:19])([F:18])[F:20])[CH:12]=2)[C:9]=1[CH3:10])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 115968194-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile

Product 1

HCID 577624434-{5-Acetyl-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-4-pyrimidinyl}benzonitrile

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4-{5-Acetyl-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-4-pyrimidinyl}benzonitrile (example 1; 100 mg, 0.24 mmol), 1-iodomethane (38.0 mg, 0.27 mmol) and potassium carbonate (34.1 mg, 0.25 mmol) are dissolved in 3 ml acetone and stirred at room temperature overnight. The solvent is removed in vacuo and the crude product is purified via preparative HPLC (RP1 8-column; eluent: aceto-nitrile-water, gradient 10:90 to 90:10).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude product is purified via preparative HPLC (RP1 8-column; eluent: aceto-nitrile-water, gradient 10:90 to 90:10)

Sources & evidence

ORD record
ord-0c727478887b4305aae4a44560e574f2
Source dataset
uspto-grants-2009_07
Patent number
US07566723B2

Reaction notes

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