Acetic Acid → HCID 178494289, compound

HRID 1708517Notes

Reaction equation

HRID 1708517 reaction equation
[CH3:1][C:2]1[C:3](N2C=NC=N2)=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.C[O-].[Na+].[C:17](O)(=[O:19])C>CO>[CH3:17][O:19][C:3]1[C:2]([CH3:1])=[CH:7][NH:6][C:5](=[O:8])[N:4]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 10942334Sodium MethoxideHCID 178430897HCID 178430897, compound

Product 1

HCID 178494289HCID 178494289, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

1.06 g (6 mmol) of 5-methyl-4-(1,2,4-triazol-1-yl)-pyrimidin-2(1H)-one are boiled under reflux with 972 mg (18 mmol) of sodium methylate in 30 ml of anhydrous methanol for 4 hours with exclusion of moisture. The cooled solution is neutralized with acetic acid, concentrated and chromatographed on silica gel using ethyl acetate/methanol 9/1. 770 mg (91.7% of theory) of 4-methoxy-5-methylpyrimidin-2(1H)-one are obtained with melting point 196°-199° C. 1H NMR (270 MHz, d6 -DMSO), δ[ppm]: 11.09 (s, 1H), 7.51 (d, 1H), 3.83 (s, 3H), 1.85 (s, 3H).

Workup

  1. concentrationconcentrated
  2. customchromatographed on silica gel

Sources & evidence

ORD record
ord-ccdff7a252dd4be3a81a86562c32d6d7
Source dataset
uspto-grants-1994_10
Patent number
US05359067

Reaction notes

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