Hydrochloric Acid → 1,6-Dihydro-4-hydroxy-1-methyl-2-methoxy-6-oxo-pyrimidine

HRID 261788Notes

Reaction equation

HRID 261788 reaction equation
[OH:1][C:2]1[N:3]=[C:4](SC)[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1.[CH3:12][OH:13].Cl>CCOCC>[OH:1][C:2]1[N:3]=[C:4]([O:13][CH3:12])[N:5]([CH3:9])[C:6](=[O:8])[CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1354085986-Hydroxy-1-methyl-2-(methylsulfanyl)pyrimidin-4(1h)-one

Product 1

HCID 1358484661,6-Dihydro-4-hydroxy-1-methyl-2-methoxy-6-oxo-pyrimidineYield 40%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 172 g (1 mol) of 1,6-dihydro-4-hydroxy-1-methyl-2-methylthio-6-oxo-pyrimidine, 700 ml of methanol and 5 ml of a solution of hydrogen chloride in ether was boiled for 10 days under reflux. The reaction mixture was then filtered while still hot and the filtrate is evaporated in vacuo. The residue was triturated with ether and the crystalline product was filtered off. In this way, 71 g (40% of theory) of 1,6-dihydro-4-hydroxy-1-methyl-2-methoxy-6-oxo-pyrimidine were obtained in the form of colorless crystals of melting point 170°-171° C. ##STR11##

Workup

  1. temperatureunder reflux
  2. filtrationThe reaction mixture was then filtered while still hot and the filtrate
  3. customis evaporated in vacuo
  4. customThe residue was triturated with ether
  5. filtrationthe crystalline product was filtered off

Sources & evidence

ORD record
ord-be41bb75b42b464f9fa7713bb4e877ed
Source dataset
uspto-grants-1979_05
Patent number
US04152426

Reaction notes

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