Methylthiouracil → 4(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-

HRID 2247848Notes

Reaction equation

HRID 2247848 reaction equation
[CH3:1][C:2]1[NH:7][C:6](=[S:8])[NH:5][C:4](=[O:9])[CH:3]=1.[Na].N1C=CC(=O)NC1=S.[Cl-].Cl[CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH+:28]([CH3:30])[CH3:29]>[O-]CC.[Na+].C(O)C>[CH3:29][N:28]([CH3:30])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[CH2:21][S:8][C:6]1[NH:5][C:4](=[O:9])[CH:3]=[C:2]([CH3:1])[N:7]=1

Participants

7

Reactant 4

HCID 667493MethylthiouracilHCID 1269845ThiouracilHCID 5360545SodiumHCID 178486212HCID 178486212, compound

Product 1

HCID 1357442584(1H)-Pyrimidinone, 2-(((2-(dimethylamino)phenyl)methyl)thio)-6-methyl-Yield 47.7%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 2723922Sodium ethoxideSolvent

Procedure

355 mg (2.5 mmol) of 6-methyl-2-thiouracil are dissolved in a sodium ethoxide solution prepared from 116 mg (5.05 mmol) of sodium metal and 15 ml of anhydrous ethanol. The mixture is gently warmed to dissolve the thiouracil, then 515 mg (2.5 mmol) of (2-chloromethylphenyl)-dimethylammonium chloride are added and the reaction mixture is refluxed under stirring for 1 hour. Sodium chloride is immediately precipitated from the solution. After evaporation under reduced pressure the residue is taken up in water, extracted 3 times with 20 ml of chloroform each, then the combined organic phase is washed with 20 ml of water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The pale yellow oily residue is rubbed with an 1:1 mixture of benzene and petroleum ether to obtain 287 mg (47.7%) of the title compound as a white crystalline product, m.p.: 151°-153° C.

Workup

  1. temperatureThe mixture is gently warmed
  2. temperaturethe reaction mixture is refluxed
  3. customSodium chloride is immediately precipitated from the solution
  4. customAfter evaporation under reduced pressure the residue
  5. extractionextracted 3 times with 20 ml of chloroform each, then the combined organic phase
  6. washis washed with 20 ml of water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. additionThe pale yellow oily residue is rubbed with an 1:1 mixture of benzene and petroleum ether

Sources & evidence

ORD record
ord-baa6d9552ea542a68ccfd12b5de6b346
Source dataset
uspto-grants-1991_08
Patent number
US05037830

Reaction notes

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