Phosphorus sulfide (P2S5) → 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-thioxo-2(1H)-pyrimidinone

HRID 65158Notes

Reaction equation

HRID 65158 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[N:16]=[C:15]([O:17]C(C)C)[N:14]([CH3:21])[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:24]>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[NH:16][C:15](=[O:17])[N:14]([CH3:21])[C:13](=[S:24])[CH:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 140965046-(3,4-dimethoxyphenyl)-2-isopropoxy-3-methyl-4(3H)-pyrimidinone

Product 1

HCID 212431973,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-thioxo-2(1H)-pyrimidinoneYield 12.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 6-(3,4-dimethoxyphenyl)-2-isopropoxy-3-methyl-4(3H)-pyrimidinone (2.5 g) and phosphorus pentasulfide (3.5 g) in pyridine (50 ml) was refluxed for 13 hours with stirring. The reaction mixture was evaporated under reduced pressure. The residue was washed with 1N-hydrochloric acid and extracted with chloroform. The extract was washed with water, dried over magnesium sulfate and evaporated under reduced pressure. The residue was triturated in ethanol and the resulting precipitate was triturated again in chloroform and collected by filtration to give 3,4-dihydro-6-(3,4-dimethoxyphenyl)-3-methyl-4-thioxo-2(1H)-pyrimidinone (0.27 g).

Workup

  1. temperaturewas refluxed for 13 hours
  2. customThe reaction mixture was evaporated under reduced pressure
  3. washThe residue was washed with 1N-hydrochloric acid
  4. extractionextracted with chloroform
  5. washThe extract was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under reduced pressure
  8. customThe residue was triturated in ethanol
  9. customthe resulting precipitate was triturated again in chloroform
  10. filtrationcollected by filtration

Sources & evidence

ORD record
ord-97e12d1cda57415db6427d737fb122aa
Source dataset
uspto-grants-1986_09
Patent number
US04612376

Reaction notes

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