Acetic Acid → HCID 178430900, compound

HRID 1708518Notes

Reaction equation

HRID 1708518 reaction equation
[CH3:1][C:2]1[C:3](N2C=NC=N2)=[N:4][C:5](=[O:8])[NH:6][CH:7]=1.[Na].C(O)(=O)C.[CH2:19]([OH:26])[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>CN(C)C=O>[CH2:19]([O:26][C:3]1[C:2]([CH3:1])=[CH:7][NH:6][C:5](=[O:8])[N:4]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 244Benzyl AlcoholHCID 5360545SodiumHCID 178430897HCID 178430897, compound

Product 1

HCID 178430900HCID 178430900, compoundYield 67.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

1.06 g (6 mmol) of 5-methyl-4-(1,2,4-triazol-1-yl)-pyrimidin-2(1H)-one are added to a solution of 2.34 g (18 mmol) of sodium benzylate in 25 ml of dry benzyl alcohol and 25 ml of dry dimethylformamide are added. The mixture is heated for 2 hours with stirring to 100° C. The cooled solution is neutralized with acetic acid, concentrated and chromatographed on silica gel using ethylacetate/methanol 9/1. 880 mg (67.9% of theory) of 4-benzyloxy-5-methylpyrimidin-2(1H)-one are obtained with melting point 181°-182°C. 1H NMR (270 MHz, d6 -DMSO), δ[ppm]: 11.14 (s, 1H), 7.56 (d, 1H), 7.41 (m, 5H), 5.35 (s, 2H), 1.87 (s, 3H).

Workup

  1. additionare added
  2. temperatureThe mixture is heated for 2 hours
  3. concentrationconcentrated
  4. customchromatographed on silica gel

Sources & evidence

ORD record
ord-e09c1aa7119c4cf185ded53f942a7bc9
Source dataset
uspto-grants-1994_10
Patent number
US05359067

Reaction notes

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