Methyl 4-methoxyacetoacetate → HCID 178494553, compound

HRID 1875908Notes

Reaction equation

HRID 1875908 reaction equation
[CH3:1][O:2][CH2:3][C:4](=O)[CH2:5][C:6]([O:8]C)=O.C(O)(=O)C.[CH:15]([NH2:17])=[NH:16].C[O-].[Na+]>CO>[CH3:1][O:2][CH2:3][C:4]1[N:17]=[CH:15][N:16]=[C:6]([OH:8])[CH:5]=1

Participants

5

Reactant 3

HCID 123500Methyl 4-methoxyacetoacetateHCID 160693Formamidine acetateHCID 10942334Sodium Methoxide

Product 1

HCID 178494553HCID 178494553, compoundYield 37.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 4-methoxy-3-oxobutanoate (3.54 mL, 26.5 mmol) in methanol (30 ml) was added formamidine acetate (3.07 g, 29.2 mmol) and sodium methoxide (13 mL, 58.4 mmol). The mixture was then heated to reflux for 18 hours and cooled to ambient temperature, then concentrated. The residue was taken up in water and the pH adjusted to 7 with 1N HCl. The aqueous mixture was extracted with chloroform. The combined organic layers were dried over magnesium sulfate, filtered and concentrated to afford 6-(methoxymethyl)pyrimidin-4-ol (1.38 g, 9.85 mmol, 37.1% yield). MS (LC/MS) R.T.=0.19; [M+H]+=141.20.

Workup

  1. temperatureThe mixture was then heated
  2. temperatureto reflux for 18 hours
  3. concentrationconcentrated
  4. extractionThe aqueous mixture was extracted with chloroform
  5. dry with materialThe combined organic layers were dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-96f33543d8134f2cb08939e5b0a1c3c1
Source dataset
uspto-grants-2012_11
Patent number
US08309577B2

Reaction notes

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