6-Methyluracil → HCID 178429729, compound

HRID 477553

Reaction equation

HRID 477553 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=O)[CH:3]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:11]>N1C=CC=CC=1>[OH:8][C:6]1[N:5]=[C:4]([SH:11])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 122836-MethyluracilHCID 14817Phosphorus sulfide (P2S5)

Product 1

HCID 178429729HCID 178429729, compoundYield 136.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

6-Methyluracil (25.0 g) was suspended in 1 liter of distilled pyridine with stirring and heated at 50° C. into solution. Phosphorus pentasulfide (12.6 g) was then added, and the mixture was refluxed for 20 hours. The solution was concentrated under reduced pressure, then the residue was refluxed with 500 ml of ethanol for one hour. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was recrystallized from ethanol, affording 5.5 g of the objective compound as colorless crystals.

Workup

  1. temperaturethe mixture was refluxed for 20 hours
  2. concentrationThe solution was concentrated under reduced pressure
  3. temperaturethe residue was refluxed with 500 ml of ethanol for one hour
  4. customInsoluble materials were removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-8803435dd1da4637b5700b006de1fda9
Source dataset
uspto-grants-1989_12
Patent number
US04888332

Linked notes

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