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

HRID 849290Notes

Reaction equation

HRID 849290 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-c1e5cb0c5e4448f7aa2dc338b5e23de4
Source dataset
uspto-grants-2000_01
Patent number
US06011158

Reaction notes

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