HCID 90051713, compound → HCID 90052172, compound

HRID 2284802Notes

Reaction equation

HRID 2284802 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH2:15][OH:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1(C)C=CC=CC=1.[O-2].[O-2].[Mn+4]>[CH2:1]([O:8][C:9]1[C:14]([CH:15]=[O:16])=[CH:13][N:12]=[C:11]([S:17][CH3:18])[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 90051713HCID 90051713, compound

Product 1

HCID 90052172HCID 90052172, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of (4-(benzyloxy)-2-(methylthio)pyrimidin-5-yl)methanol (S26, 818 mg) in toluene (30 mL), manganese dioxide (8.13 g) was added at room temperature, and the mixture was stirred at 50° C. for 1 hour. The reaction mixture was cooled to room temperature, and then the insoluble matter was removed by filtration through Cerite. The solvent was evaporated under reduced pressure to obtain oily 4-(benzyloxy)-2-(methylthio)pyrimidine-5-carbaldehyde (S20, 666 mg).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe insoluble matter was removed by filtration through Cerite
  3. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-21d607f6fe1347b294c52ed57a7f3e7f
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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