Methyl iodide → Ethyl 4-(4-cyano-2-methylphenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoro-methyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

HRID 1921140Notes

Reaction equation

HRID 1921140 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11](=[S:31])[NH:10]2)=[C:5]([CH3:32])[CH:4]=1)#[N:2].IC.[C:35](=O)([O-])[O-].[K+].[K+]>CC(C)=O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[C:13]([CH3:20])[N:12]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([C:27]([F:30])([F:29])[F:28])[CH:22]=3)[C:11]([S:31][CH3:35])=[N:10]2)=[C:5]([CH3:32])[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 57762430Ethyl 4-(4-cyano-2-methylphenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Product 1

HCID 57762462Ethyl 4-(4-cyano-2-methylphenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoro-methyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl 4-(4-cyano-2-methylphenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate Example 21; 100 mg, 0.22 mmol), 1-iodomethane (34.0 mg, 0.24 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 (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10).

Workup

  1. customThe solvent is removed in vacuo
  2. customthe crude product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)

Sources & evidence

ORD record
ord-4b5e40cab3054157abdaf3e5126c2f82
Source dataset
uspto-grants-2012_05
Patent number
US08173665B2

Reaction notes

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