Methyl 4-methoxyacetoacetate → HCID 178494553, compound

HRID 250042Notes

Reaction equation

HRID 250042 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-128180baf0ba44ec9c65366ff0ed33cf
Source dataset
uspto-grants-2011_01
Patent number
US07863291B2

Reaction notes

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