Methanol → 2,4,6-Trimethoxy-5-(methylsulfanyl)pyrimidine

HRID 1719512Notes

Reaction equation

HRID 1719512 reaction equation
Cl[C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([O:10][CH3:11])[C:3]=1[S:12][CH3:13].[CH3:14][OH:15].[OH-].[K+]>O>[CH3:13][S:12][C:3]1[C:4]([O:10][CH3:11])=[N:5][C:6]([O:8][CH3:9])=[N:7][C:2]=1[O:15][CH3:14]

Participants

5

Reactant 3

HCID 887MethanolHCID 14797Potassium HydroxideHCID 155903704-Chloro-2,6-dimethoxy-5-(methylsulfanyl)pyrimidine

Product 1

HCID 155903712,4,6-Trimethoxy-5-(methylsulfanyl)pyrimidine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Charged into a 100-milliliter, 4-necked flask equipped with a reflux condenser, thermometer and stirrer were 2.2 g of 6-chloro-2,4-dimethoxy-5-methylthiopyrimidine and 40 ml of methanol. They were stirred into a homogeneous solution. Subsequent to an addition of 2.0 g of potassium hydroxide, the resultant mixture was heated and refluxed, with thorough stirring, for 3 hours. The liquid reaction mixture was then poured into water and the resultant solid precipitate was collected by filtration. It was recrystallized from isopropyl alcohol, thereby obtaining 5-methylthio-2,4,6-trimethoxypyrimidine (m.p. 90°-91° C.). Yield: 1.96 g(90.7%).

Workup

  1. additionCharged into a 100-milliliter, 4-necked flask
  2. customequipped with a reflux condenser
  3. customthermometer and stirrer were
  4. temperaturerefluxed, with thorough stirring, for 3 hours
  5. customThe liquid reaction mixture
  6. filtrationthe resultant solid precipitate was collected by filtration
  7. customIt was recrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-5200ee52dbcb4c3fbcb2c98c0c89c2c2
Source dataset
uspto-grants-1985_09
Patent number
US04540698

Reaction notes

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