Potassium Carbonate → 2-(4-bromo-2-dimethylaminobenzyl)thio-6-methyl-4(3H)-pyrimidinone

HRID 2247854Notes

Reaction equation

HRID 2247854 reaction equation
[Cl-].[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:12]Cl)=[C:7]([NH+:9]([CH3:11])[CH3:10])[CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:20][C:21]1[NH:26][C:25](=[S:27])[NH:24][C:23](=[O:28])[CH:22]=1>CN(C)C(=O)C>[Br:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:12][S:27][C:25]2[NH:24][C:23](=[O:28])[CH:22]=[C:21]([CH3:20])[N:26]=2)=[C:7]([N:9]([CH3:11])[CH3:10])[CH:8]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 667493MethylthiouracilHCID 19816071(5-Bromo-2-chloromethylphenyl)dimethylammonium chloride

Product 1

HCID 1355591812-(4-bromo-2-dimethylaminobenzyl)thio-6-methyl-4(3H)-pyrimidinoneYield 49.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Conditions

Temperature
100 °C

Procedure

1.0 g (3.5 mmol) of (5-bromo-2-chloromethylphenyl)dimethylammonium chloride (m.p.: 118°-120° C.) and 0.97 g (7.0 mmol) of anhydrous potassium carbonate are added to the solution of 0.45 g (3.2 mmol) of 6-methyl-2-thiouracil in 15 ml of N,N-dimethylacetamide and the reaction mixture is stirred in an oil bath of 100° C. temperature for 3 hours. After cooling to room temperature the inorganic salts are filtered and the filtrate is evaporated under reduced pressure. The evaporation residue is shaken with the mixture of 5 ml of water and 5 ml of chloroform and after separation the organic phase is extracted 4 times with 5 ml of chloroform each. The combined organic phase is washed with water, dried over anhydrous magnesium sulfate and evaporated. The oily residue is purified by chromatography on a silica gel column by using a 4:1 mixture of ethyl acetate/benzene as eluent. The pure fractions are evaporated under reduced pressure and the residue is recrystallized from ethanol to give 0.56 g (49.5%) of the title compound as a white crystalline product, m.p.: 163°-164° C.

Workup

  1. temperatureAfter cooling to room temperature the inorganic salts
  2. filtrationare filtered
  3. customthe filtrate is evaporated under reduced pressure
  4. stirringThe evaporation residue is shaken with the mixture of 5 ml of water and 5 ml of chloroform
  5. customafter separation the organic phase
  6. extractionis extracted 4 times with 5 ml of chloroform each
  7. washThe combined organic phase is washed with water
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customevaporated
  10. customThe oily residue is purified by chromatography on a silica gel column
  11. additiona 4:1 mixture of ethyl acetate/benzene as eluent
  12. customThe pure fractions are evaporated under reduced pressure
  13. customthe residue is recrystallized from ethanol

Sources & evidence

ORD record
ord-57129a23eae84afcb7b4bc5a296a2c46
Source dataset
uspto-grants-1991_08
Patent number
US05037830

Reaction notes

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