HCID 178469211, compound → HCID 15147484, compound

HRID 255707Notes

Reaction equation

HRID 255707 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[NH:5][CH:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[N:3]=[C:4]([C:19]2[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=2)[N:5]=[C:6]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:7]=1[C:8]([O:10][CH2:11][CH3:12])=[O:9]

Participants

4

Reactant 1

HCID 178469211HCID 178469211, compound

Product 1

HCID 15147484HCID 15147484, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of ethyl 4-methyl-2-phenyl-6-(4-pyridyl)-1,6-dihydro-5-pyrimidinecarboxylate (13.4 g) in chloroform (300 ml) was added activated manganese dioxide (53.6 g) and the mixture was refluxed for two hours with stirring vigorously. After allowing to cool to room temperature, manganese dioxide was filtered off. The filtrate was evaporated in vacuo and the residual precipitate was recrystallized from a mixture of ether (80 ml) and petroleum ether (40 ml). The crystal was filtered off, washed with ether and dried in vacuo to give ethyl 6-methyl-2-phenyl-4-(4-pyridyl)-5-pyrimidinecarboxylate (7.5 g).

Workup

  1. temperaturethe mixture was refluxed for two hours
  2. filtrationmanganese dioxide was filtered off
  3. customThe filtrate was evaporated in vacuo
  4. customthe residual precipitate was recrystallized from a mixture of ether (80 ml) and petroleum ether (40 ml)
  5. filtrationThe crystal was filtered off
  6. washwashed with ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-98a9842b6ec34f1f8a506c12471d6710
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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