Ethanol → 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-thioxo-2(1H)-pyrimidinone

HRID 65159Notes

Reaction equation

HRID 65159 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=[O:17])[N:14]([CH3:18])[C:13](=O)[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:21].C(O)C>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=[O:17])[N:14]([CH3:18])[C:13](=[S:21])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 702EthanolHCID 14817Phosphorus sulfide (P2S5)HCID 137142586-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 212431973,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-thioxo-2(1H)-pyrimidinoneYield 106.9%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a suspension of 6-(3,4-dimethoxyphenyl)-3-methyl-2,4(1H,3H)-pyrimidinedione (1.5 g) in dioxane (15 ml) was added phosphorus pentasulfide (1.27 g) and the mixture was refluxed for 2 hours. After being cooled, ethanol (15 ml) was added thereto, and the mixture was refluxed for 2 hours again. After being cooled, the resulting precipitates were collected by filtration and washed successively with ethanol and diisopropyl ether to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-thioxo-2(1H)-pyrimidinone (0.85 g).

Workup

  1. temperaturethe mixture was refluxed for 2 hours
  2. temperatureAfter being cooled
  3. temperaturethe mixture was refluxed for 2 hours again
  4. temperatureAfter being cooled
  5. customthe resulting precipitates
  6. filtrationwere collected by filtration
  7. washwashed successively with ethanol and diisopropyl ether

Sources & evidence

ORD record
ord-321924017ef641a18ed0ee79e964dc09
Source dataset
uspto-grants-1986_09
Patent number
US04612376

Reaction notes

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