Methyl 2-acetylheptanoate → 2-(furan-2-ylmethyl)-6-methyl-5-pentyl-1H-pyrimidin-4-one

HRID 1033042Notes

Reaction equation

HRID 1033042 reaction equation
Cl.[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]([NH2:10])=[NH:9].[C:11]([CH:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15](OC)=[O:16])(=O)[CH3:12].C[O-].[Na+]>CO>[O:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[CH2:7][C:8]1[NH:10][C:11]([CH3:12])=[C:14]([CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:15](=[O:16])[N:9]=1

Participants

5

Reactant 3

HCID 10511765Methyl 2-acetylheptanoateHCID 10942334Sodium MethoxideHCID 190863002-(Furan-2-yl)acetamidine hydrochloride

Product 1

HCID 1784422172-(furan-2-ylmethyl)-6-methyl-5-pentyl-1H-pyrimidin-4-oneYield 37.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The mixture of 2-(furan-2-yl)acetamidine hydrochloride (30.0 g), methyl 2-acetylheptanoate (34.8 g) and sodium methoxide (10.1 g) in methanol (300 ml) was stirred for 4.5 hours at ambient temperature, and then the solvent was removed by concentration. To the residue was added a mixture of ethyl acetate and water, and the mixture was adjusted to pH 9 with 6N-hydrochloric acid. The separated organic layer was washed with brine and dried over magnesium sulfate. Evaporation of the solvent gave a residue, which was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (19:1, V/V). The eluted fractions containing the desired product were collected and evaporated in vacuo to give 2-(furan-2-ylmethyl)-6-methyl-5-n-pentyl-4(1H)pyrimidinone (18.18 g).

Workup

  1. customthe solvent was removed by concentration
  2. additionTo the residue was added
  3. additiona mixture of ethyl acetate and water
  4. washThe separated organic layer was washed with brine
  5. dry with materialdried over magnesium sulfate
  6. customEvaporation of the solvent
  7. customgave a residue, which
  8. customwas purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (19:1, V/V)
  9. additionThe eluted fractions containing the desired product
  10. customwere collected
  11. customevaporated in vacuo

Sources & evidence

ORD record
ord-1bda8400f4e54d85afce3cc443c2ecc5
Source dataset
uspto-grants-1994_05
Patent number
US05308857

Reaction notes

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