Diethyl (ethoxymethylene)malonate → 6-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

HRID 2257101Notes

Reaction equation

HRID 2257101 reaction equation
C([O:3][CH:4]=[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6](OCC)=O)C.C(O)(=O)C.[CH:20]([NH2:22])=[NH:21]>C(O)C.C(OCC)(=O)C.Cl>[NH:22]1[C:4](=[O:3])[C:5]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:6][N:21]=[CH:20]1

Participants

6

Reactant 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 160693Formamidine acetate

Product 1

HCID 963476-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl esterYield 40%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Diethyl ethoxymethylenemalonate (10.1 mL, 50 mmole) and formamidine acetate (10.4 g, 100 mmole) were refluxed in ethanol (10 mL) for 24 hours. The reaction mixture was allowed to cool to room temperature overnight, and suspended in ethyl acetate (30 mL) and 1.0N HCl (20 mL). The suspension was filtered, and the filter cake was washed with 1.0N HCl, followed by water, then ethyl acetate, and air dried affording the title compound as an tan solid (3.33 g, 40% yield). Rf =0.21 (silica gel, 10% methanol in dichloromethane). m.p. 187°-188° C.

Workup

  1. filtrationThe suspension was filtered
  2. washthe filter cake was washed with 1.0N HCl
  3. dry with materialethyl acetate, and air dried

Sources & evidence

ORD record
ord-990936d2ca454d678f447494b2ca2422
Source dataset
uspto-grants-1997_08
Patent number
US05656645

Reaction notes

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