HCID 178418551, compound → Methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylate

HRID 4671Notes

Reaction equation

HRID 4671 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[NH:5][CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]>C(Cl)(Cl)Cl.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[N:3]=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[N:5]=[C:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-:20])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]

Participants

4

Reactant 1

HCID 178418551HCID 178418551, compound

Product 1

HCID 15147475Methyl 6-methyl-2-phenyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylateYield 67.8%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 6212ChloroformSolvent

Procedure

To a solution of methyl 4-methyl-2-phenyl-6-(3-nitrophenyl)-1,6-dihydro-5-pyrimidinecarboxylate (475 g) in chloroform (5 l) was added activated manganese dioxide (1.9 kg) 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 diisopropyl ether (500 ml). The crystal was filtered off, washed with diisopropyl ether and dried in vacuo to give methyl 6-methyl-4-(3-nitrophenyl)-2-phenyl-5-pyrimidinecarboxylate (320 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 diisopropyl ether (500 ml)
  5. filtrationThe crystal was filtered off
  6. washwashed with diisopropyl ether
  7. customdried in vacuo

Sources & evidence

ORD record
ord-3d49eb61e2fd44989265dbcff16dd028
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Reaction notes

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