Hydrochloric Acid → 6-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

HRID 1038969Notes

Reaction equation

HRID 1038969 reaction equation
Cl.[CH:2]([NH2:4])=[NH:3].C([O:7][CH:8]=[C:9]([C:15](OCC)=O)[C:10]([O:12][CH2:13][CH3:14])=[O:11])C.C(OCC)(=O)C.Cl>C(O)C.O>[O:7]=[C:8]1[NH:4][CH:2]=[N:3][CH:15]=[C:9]1[C:10]([O:12][CH2:13][CH3:14])=[O:11]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6871Diethyl (ethoxymethylene)malonateHCID 8857Ethyl AcetateHCID 10313058Methanimidamide, hydrochloride (1:1)

Product 1

HCID 963476-Oxo-1,6-dihydro-pyrimidine-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of formamidine hydrochloride (4.02 g, 49.9 mmol) and diethyl ethoxymethylenemalonate (5 ml, 24.95 mmol) in ethanol (4.99 ml) was heated to 120° C. (by microwave irradiation) for 15 h. After the reaction mixture was cooled to room temperature, ethyl acetate, hydrochloric acid (1M), and water were added. The aqueous layer was washed with ethyl acetate and then extracted with 3:1 chloroform:isopropanol. The combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure to afford ethyl 6-oxo-1,6-dihydropyrimidine-5-carboxylate as an orange solid. LRMS (ESI) calc'd for (C7H9N2O3) [M+H]+, 169.1; found 169.1.

Workup

  1. custom(by microwave irradiation) for 15 h
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. washThe aqueous layer was washed with ethyl acetate
  4. extractionextracted with 3:1 chloroform
  5. dry with materialThe combined organic extracts were dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c927a47ce03d44228d7563403e097ce6
Source dataset
uspto-grants-2013_10
Patent number
US08552019B2

Reaction notes

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