Acetic Acid → HCID 178477360, compound

HRID 1708519Notes

Reaction equation

HRID 1708519 reaction equation
[H-].[Na+].[CH2:3]([SH:5])[CH3:4].[CH3:6][C:7]1[C:8](N2C=NC=N2)=[N:9][C:10](=[O:13])[NH:11][CH:12]=1.C(O)(=O)C>CN(C)C=O>[CH2:3]([S:5][C:8]1[C:7]([CH3:6])=[CH:12][NH:11][C:10](=[O:13])[N:9]=1)[CH3:4]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 178430897HCID 178430897, compound

Product 1

HCID 178477360HCID 178477360, compoundYield 62.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

786 mg (18 mmol) of a 55% strength sodium hydride emulsion are added to 0.7 ml (9 mmol) of ethylmercaptan in 25 ml of dry dimethylformamide at 0° C. and the mixture is stirred for 30 minutes at 0° C. 1.06 g (6 mmol) of 5-methyl-4-(1,2,4-triazol-1-yl)-pyrimidin-2(1H)-one are then added and the mixture is stirred for 3 hours at room temperature. The reaction mixture is neutralized by addition of acetic acid, concentrated and chromatographed on silica gel using dichloromethane/methanol 20/1. 0.64 g (62.7% of theory) of 4-ethylthio-5-methylpyrimidin-2(1H)-one is obtained with melting point 181°-184° C. 1H NMR (60 MHz, d6 -DMSO), δ[ppm]: 11.45 (s, 1H), 7.55 (s, 1H), 3.10 (q, 2H), 1.90 (s, 3H), 1.25 (t, 3H).

Workup

  1. stirringthe mixture is stirred for 3 hours at room temperature
  2. concentrationconcentrated
  3. customchromatographed on silica gel

Sources & evidence

ORD record
ord-411021e0eb5d4b53bc8f5d56d0071964
Source dataset
uspto-grants-1994_10
Patent number
US05359067

Reaction notes

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