Benzamidine, hydrochloride → Ethyl 4-(2-chlorophenyl)-2-phenyl-5-pyrimidinecarboxylate

HRID 1440787Notes

Reaction equation

HRID 1440787 reaction equation
Cl.[C:2]([NH2:10])(=[NH:9])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[O-]CC.[Na+].[Cl:15][C:16]1[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=1[C:18]([C:20](=[CH:26]N(C)C)[C:21]([O:23][CH2:24][CH3:25])=[O:22])=O>C(O)C>[Cl:15][C:16]1[CH:33]=[CH:32][CH:31]=[CH:30][C:17]=1[C:18]1[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[CH:26][N:10]=[C:2]([C:3]2[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=2)[N:9]=1

Participants

5

Reactant 3

HCID 80289Benzamidine, hydrochlorideHCID 2723922Sodium ethoxideHCID 54509863Ethyl 2-(2-chlorobenzoyl)-3-dimethylaminopropenoate

Product 1

HCID 18981984Ethyl 4-(2-chlorophenyl)-2-phenyl-5-pyrimidinecarboxylateYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirred solution of 3.45 g of benzamidine hydrochloride in 50 cc of ethanol was added 1.50 g of sodium ethoxide at room temperature and the mixture was stirred for 10 minutes. The resulting suspension was added to 6.2 g of compound D in 50 cc of ethanol and the resulting mixture was heated under reflux for 6 hours. After cooling, the solvent was distilled off, and AcOEt and water were added to the residue. The organic layer was further washed with a saturated aqueous sodium bicarbonate solution and dried over magnesium sulfate. The solvent was distilled off and the crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/8) to obtain 5.80 g of compound E. Yield: 77.6%.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off
  5. additionAcOEt and water were added to the residue
  6. washThe organic layer was further washed with a saturated aqueous sodium bicarbonate solution
  7. dry with materialdried over magnesium sulfate
  8. distillationThe solvent was distilled off
  9. customthe crude product thus obtained
  10. customwas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/8)

Sources & evidence

ORD record
ord-9dd31b38862b4f1da30f5edf315d4cde
Source dataset
uspto-grants-1996_03
Patent number
US05500424

Reaction notes

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