5-Hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine → HCID 9996051, compound

HRID 4681Notes

Reaction equation

HRID 4681 reaction equation
[OH:1][CH2:2][C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[N:5][C:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[N:7][C:8]=1[CH3:9]>C(OCC)(=O)C.[O-2].[O-2].[Mn+4]>[CH:2]([C:3]1[C:4]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([N+:22]([O-:24])=[O:23])[CH:17]=2)=[N:5][C:6]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[N:7][C:8]=1[CH3:9])=[O:1]

Participants

4

Reactant 1

HCID 103361765-Hydroxymethyl-6-methyl-2-phenyl-4-(3-nitrophenyl)pyrimidine

Product 1

HCID 9996051HCID 9996051, compoundYield 50.3%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-hydroxymethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.3 g) in ethyl acetate (10 ml) was added activated manganese dioxide (2.4 g) and the mixture was refluxed for 2 hours under stirring vigorously. After allowing to stand to room temperature, manganese dioxide was filtered off. The filtrate was evaporated in vacuo, and the residual precipitate was recrystallized from diethyl ether to give 5-formyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (0.15 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. customto stand to room temperature
  3. filtrationmanganese dioxide was filtered off
  4. customThe filtrate was evaporated in vacuo
  5. customthe residual precipitate was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-58f90a0544c441568e26fdbf9e238eb3
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Reaction notes

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