Sodium → 5-Propyl-2-(4-trifluoromethylphenyl)pyrimidine

HRID 1788641Notes

Reaction equation

HRID 1788641 reaction equation
Cl.[F:2][C:3]([F:14])([F:13])[C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH2:10])=[NH:9])=[CH:6][CH:5]=1.C[O-].[Na+].[Na]>CO>[CH2:5]([C:4]1[CH:3]=[N:9][C:8]([C:7]2[CH:11]=[CH:12][C:4]([C:3]([F:13])([F:14])[F:2])=[CH:5][CH:6]=2)=[N:10][CH:12]=1)[CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10942334Sodium MethoxideHCID 125357914-(Trifluoromethyl)benzamidine Hydrochloride

Product 1

HCID 139315715-Propyl-2-(4-trifluoromethylphenyl)pyrimidineYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

4-Trifluoromethylbenzamidine hydrochloride (5 g, 0.02 mol) and α-propyl-β-dimethylaminoacrolein (3 g, 0.02 mol) were added to a sodium methylate solution having metallic sodium (1 g) dissolved in anhydrous methanol (50 ml), followed by boiling the mixture for 4 hours with stirring, distilling off methanol, adding toluene (50 ml) to the reaction residue to extract the product, washing the resulting extract with water, drying the toluene layer with anhydrous sodium sulfate, distilling off toulene and three times recrystallizing the residue from methanol to obtain 5-propyl-2-(4-trifluoromethylphenyl)pyrimidine (3 g, 0.01 mol).

Workup

  1. customfor 4 hours
  2. distillationdistilling off methanol
  3. additionadding toluene (50 ml) to the reaction residue
  4. extractionto extract the product
  5. washwashing the resulting
  6. extractionextract with water
  7. dry with materialdrying the toluene layer with anhydrous sodium sulfate
  8. distillationdistilling off toulene and three times
  9. customrecrystallizing the residue from methanol

Sources & evidence

ORD record
ord-a5ca049c5eda4598a16a6e6dcc623604
Source dataset
uspto-grants-1987_08
Patent number
US04684476

Reaction notes

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