Sodium Methoxide → Methyl 4-(4-cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)-phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

HRID 1921129Notes

Reaction equation

HRID 1921129 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:14]([C:15]([O:17][CH2:18]C)=[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][CH3:32])=[N:10]2)=[CH:5][CH:4]=1)#[N:2].C[O-].[Na+]>CO>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:14]([C:15]([O:17][CH3:18])=[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][CH3:32])=[N:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 57762474Ethyl 4-(4-cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

Product 1

HCID 57762469Methyl 4-(4-cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)-phenyl]-1,4-dihydro-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 4-(4-cyanophenyl)-6-methyl-2-(methylsulfanyl)-1-[3-(trifluoromethyl)phenyl]-1,4-dihydro-5-pyrimidinecarboxylate (example 7; 100 mg, 0.22 mmol) and sodium methoxide (117.6 mg, 2.18 mmol) are dissolved in 5 ml methanol and stirred at reflux temperature for 3 h. The reaction is quenched with 10 ml of water and the aqueous phase is extracted with 10 ml methylene chloride (2×). After drying with sodium sulfate, the solvent is removed in vacuo and the product is purified by column chromatography (silica gel; eluent: cyclohexane-ethyl acetate, gradient 90:10 to 50:50).

Workup

  1. temperatureat reflux temperature for 3 h
  2. customThe reaction is quenched with 10 ml of water
  3. extractionthe aqueous phase is extracted with 10 ml methylene chloride (2×)
  4. dry with materialAfter drying with sodium sulfate
  5. customthe solvent is removed in vacuo
  6. customthe product is purified by column chromatography (silica gel; eluent: cyclohexane-ethyl acetate, gradient 90:10 to 50:50)

Sources & evidence

ORD record
ord-738eda09bc6e4bc1b86a1754059d3a9e
Source dataset
uspto-grants-2012_05
Patent number
US08173665B2

Reaction notes

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