Water → 2-[(3,5-dimethyl-4-methoxypyridin-2-yl)methyl]thio-6-methyl-4(3H)-pyrimidinone

HRID 2247855Notes

Reaction equation

HRID 2247855 reaction equation
[OH-].[K+].O.[CH3:4][C:5]1[NH:10][C:9](=[S:11])[NH:8][C:7](=[O:12])[CH:6]=1.[Cl-].Cl[CH2:15][C:16]1[C:21]([CH3:22])=[C:20]([O:23][CH3:24])[C:19]([CH3:25])=[CH:18][NH+:17]=1>C(O)C>[CH3:22][C:21]1[C:16]([CH2:15][S:11][C:9]2[NH:8][C:7](=[O:12])[CH:6]=[C:5]([CH3:4])[N:10]=2)=[N:17][CH:18]=[C:19]([CH3:25])[C:20]=1[O:23][CH3:24]

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 667493MethylthiouracilHCID 459256972-(Chloromethyl)-4-methoxy-3,5-dimethylpyridin-1-ium chloride

Product 1

HCID 1355591852-[(3,5-dimethyl-4-methoxypyridin-2-yl)methyl]thio-6-methyl-4(3H)-pyrimidinoneYield 36%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

After dissolving 0.22 g (4.0 mmol) of potassium hydroxide in the mixture of 15 ml of ethanol and 3 ml of water, first 0.28 g (2.0 mmol) of 6-methyl-2-thiouracil, then a solution of 0.44 g (2.0 mmol) of 2-chloromethyl-3,5-dimethyl-4-methoxypyridinium chloride (m.p.: 127°-128° C.) in 15 ml of ethanol are added. The reaction mixture is stirred at room temperature for 20 hours, then ethanol is evaporated under reduced pressure, 10 ml of water are added to the residue and the product is extracted 3 times with 5 ml of chloroform each. The combined organic phase is washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue is recrystallized from 2-propanol to obtain 0.21 g (36%) of the title compound as a white crystalline product, m.p.: 231°-233° C.

Workup

  1. customethanol is evaporated under reduced pressure, 10 ml of water
  2. additionare added to the residue
  3. extractionthe product is extracted 3 times with 5 ml of chloroform each
  4. washThe combined organic phase is washed with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customevaporated under reduced pressure
  7. customThe residue is recrystallized from 2-propanol

Sources & evidence

ORD record
ord-48b8c66ff79d4cc18b4b20a622b10b48
Source dataset
uspto-grants-1991_08
Patent number
US05037830

Reaction notes

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