Acetic Acid → HCID 20240522, compound

HRID 364232Notes

Reaction equation

HRID 364232 reaction equation
[NH2:1][CH2:2][C:3]1[N:8]=[C:7]([S:9][CH3:10])[N:6]=[C:5]([O:11][CH3:12])[CH:4]=1.[C:13](O)(=[O:15])[CH3:14]>[OH-].[Na+]>[C:13]([NH:1][CH2:2][C:3]1[N:8]=[C:7]([S:9][CH3:10])[N:6]=[C:5]([O:11][CH3:12])[CH:4]=1)(=[O:15])[CH3:14]

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 13377336HCID 13377336, compound

Product 1

HCID 20240522HCID 20240522, compound

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

A mixture of 3.05 g (16.5 mmole) of 6-aminomethyl-4-methoxy-2-methylthiopyrimidine (from Example 4) and 50 ml of glacial acetic acid was heated at reflux for 16 hours, and was then evaporated. The residue obtained was dissolved in 20 ml of five percent aqueous sodium hydroxide solution and extracted with four 30 ml portions of chloroform. The combined extracts were washed twice with 30 ml portions of water and then with 30 ml of saturated aqueous sodium chloride solution. The combined extracts were then dried over magnesium sulfate and evaporated to provide 6-acetylaminomethyl-4-methoxy-2-methylthiopyrimidine as an off-white solid. The structural assignment was confirmed by infrared and nuclear magnetic resonance spectral analyses.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 16 hours
  3. customwas then evaporated
  4. customThe residue obtained
  5. extractionextracted with four 30 ml portions of chloroform
  6. washThe combined extracts were washed twice with 30 ml portions of water
  7. dry with materialThe combined extracts were then dried over magnesium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-c52e8da9f85e4cb3968596a0abead297
Source dataset
uspto-grants-1986_08
Patent number
US04604466

Reaction notes

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