Water → HCID 14276132, compound

HRID 1165203Notes

Reaction equation

HRID 1165203 reaction equation
[Br:1][C:2]1[C:3](=[O:14])[N:4]([CH:11]([CH3:13])[CH3:12])[C:5]([S:9][CH3:10])=[N:6][C:7]=1[OH:8].[Cl:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20]Br)=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:14])[N:4]([CH:11]([CH3:12])[CH3:13])[C:5]([S:9][CH3:10])=[N:6][C:7]=1[O:8][CH2:20][C:19]1[CH:22]=[CH:23][C:16]([Cl:15])=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 693291-(Bromomethyl)-4-chlorobenzeneHCID 135847647HCID 135847647, compound

Product 1

HCID 14276132HCID 14276132, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 20 ml of N,N-dimethylformamide were dissolved 1.0 g of 5-bromo-6-hydroxy-2-methylthio-3-i-propyl-4(3H)-pyrimidinone and 0.74 g of 4-chlorobenzylbromide, and then 1 g of potassium carbonate was added thereto. The mixture was subjected to a reaction at 80° C. for 3 hours. After allowing to cool in air, the resulting solution was poured into 50 ml of water and then extracted twice with 30 ml of ethyl ether. The ethyl ether layer was washed with water, dried over anhydrous sodium sulfate and freed of solvent by distillation under reduced pressure to give 1.25 g of a crude product. The product was purified by means of column chromatography (on silica gel, eluting with benzene) to give 0.8 g of the intended product as an oil.

Workup

  1. customThe mixture was subjected to a reaction at 80° C. for 3 hours
  2. temperatureto cool in air
  3. extractionextracted twice with 30 ml of ethyl ether
  4. washThe ethyl ether layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationfreed of solvent by distillation under reduced pressure
  7. customto give 1.25 g of a crude product
  8. customThe product was purified by means of column chromatography (on silica gel, eluting with benzene)

Sources & evidence

ORD record
ord-c51f69463cdd4991a38d73085ee1e7d8
Source dataset
uspto-grants-1990_03
Patent number
US04908379

Reaction notes

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