Acetic Acid → 5-(2-Hydroxyethyl)-2,6-dimethylpyrimidin-4-ol

HRID 580894Notes

Reaction equation

HRID 580894 reaction equation
[C:1]([CH:4]1[CH2:8][CH2:7][O:6][C:5]1=[O:9])(=O)[CH3:2].Cl.[C:11]([NH2:14])(=[NH:13])[CH3:12].C[O-].[Na+].C(O)(=O)C>CO>[OH:6][CH2:7][CH2:8][C:4]1[C:5](=[O:9])[NH:14][C:11]([CH3:12])=[N:13][C:1]=1[CH3:2]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 106012-AcetylbutyrolactoneHCID 67170Acetamidine monohydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 1354593675-(2-Hydroxyethyl)-2,6-dimethylpyrimidin-4-olYield 22.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

3-acetyldihydro-2(3H)-furanone (25.6 g) was added to a stirred mixture of acetamidine hydrochloride (20 g) and sodium methylate (110 g) in methanol (150 ml). The reaction mixture was stirred and refluxed overnight. The reaction mixture was cooled and acetic acid (36 g) was added dropwise. The precipitate was filtered off and the filtrate evaporated. The residue was purified by column chromatography over silica gel (eluent: CHCl3 /(CH3OH/NH3) 90/10). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanol. The crystals were filtered off and dried, yielding 7.6 g (22%) of 5-(2-hydroxyethyl)-2,6-dimethyl-4(3H)-pyrimidinone (intermediate 4).

Workup

  1. temperaturerefluxed overnight
  2. temperatureThe reaction mixture was cooled
  3. filtrationThe precipitate was filtered off
  4. customthe filtrate evaporated
  5. customThe residue was purified by column chromatography over silica gel (eluent: CHCl3 /(CH3OH/NH3) 90/10)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customThe residue was crystallized from 2-propanol
  9. filtrationThe crystals were filtered off
  10. customdried

Sources & evidence

ORD record
ord-f225ee5dca754a558fa1d97e189ebcbb
Source dataset
uspto-grants-1999_07
Patent number
US05919788

Reaction notes

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