Potassium Carbonate → Ethyl 4-(4-cyanophenyl)-2-{[2-(diethylamino)ethyl]sulfanyl}-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

HRID 230279Notes

Reaction equation

HRID 230279 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)=[CH:5][CH:4]=1)#[N:2].Br.Br[CH2:34][CH2:35][N:36]([CH2:39][CH3:40])[CH2:37][CH3:38].C(=O)([O-])[O-].[K+].[K+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CC(C)=O>[C:1]([C:3]1[CH:4]=[CH:5][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][CH2:34][CH2:35][N:36]([CH2:39][CH3:40])[CH2:37][CH3:38])=[N:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 706072-Bromoethyldiethylammonium bromideHCID 57762441Ethyl 4-(4-cyanophenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate

Product 1

HCID 57762467Ethyl 4-(4-cyanophenyl)-2-{[2-(diethylamino)ethyl]sulfanyl}-6-methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 180AcetoneSolvent

Procedure

Ethyl 4-(4-cyanophenyl)-6-methyl-2-thioxo-1-[3-(trifluoromethyl)phenyl]-1,2,3,4-tetrahydro-5-pyrimidinecarboxylate (Example 3; 100 mg, 0.22 mmol), N-(2-bromo-ethyl)-N,N-diethylamine hydrobromide (64.5 mg, 0.25 mmol), N,N,N-tributyl-1-butanaminium iodide (7 mg, 0.03 mmol) and potassium carbonate (65.2 mg, 0.47 mmol) are dissolved in 3 ml acetone and stirred at room temperature overnight. The solvent is removed in vacuo and the 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 product is purified via preparative HPLC (RP18-column; eluent: acetonitrile-water, gradient 10:90 to 90:10)

Sources & evidence

ORD record
ord-142b5ef67b81496882a7584b02a65172
Source dataset
uspto-grants-2009_07
Patent number
US07566723B2

Reaction notes

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