Diethyl (ethoxymethylene)malonate → Ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylate

HRID 2257957

Reaktionsgleichung

Reaktionsgleichung von HRID 2257957
C(O)(=O)C.[C:5]([NH2:8])(=[NH:7])[CH3:6].C([O:11][CH:12]=[C:13]([C:19](OCC)=O)[C:14]([O:16][CH2:17][CH3:18])=[O:15])C>C(O)C.O.ClCCl>[CH3:6][C:5]1[NH:7][C:12](=[O:11])[C:13]([C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:19][N:8]=1

Komponenten

6

Edukt 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 160356Ethanimidamide, acetate (1:1)2×

Produkt 1

HCID 293750Ethyl 4-hydroxy-2-methylpyrimidine-5-carboxylateAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Acetamidine acetate (37.21 g, 0.31 mole) and diethyl ethoxymethylenemalonate (63 mL, 0.31 mole) were refluxed for 4 h in ethanol (60 mL). The reaction mixture was allowed to cool for 15 min., then acetamidine acetate (37.21 g, 0.31 mole) was added. The reaction mixture was refluxed for 22 hours, allowed to cool to room temperature, and diluted with water (200 mL) and dichloromethane (200 mL). The aqueous layer was extracted with 10% isopropanol/dichloromethane (2×200 mL). The combined organic extracts were washed with water (50 mL), brine (50 mL), dried over magnesium sulfate, filtered and the solvent was removed. The residue was recrystallized from chloroform/hexanes in two crops to afford the title compound (24.92 g) in 46% yield as yellowish crystals. Rf =0.27 (silica gel, 10% isopropanol in dichloromethane). m.p. 187°-188° C.

Aufarbeitung

  1. temperatureto cool for 15 min.
  2. temperatureThe reaction mixture was refluxed for 22 hours
  3. extractionThe aqueous layer was extracted with 10% isopropanol/dichloromethane (2×200 mL)
  4. washThe combined organic extracts were washed with water (50 mL), brine (50 mL)
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. customthe solvent was removed
  8. customThe residue was recrystallized from chloroform/hexanes in two crops

Quellen und Nachweise

ORD-Eintrag
ord-e491466fcd1449ceaaf2476c667addf5
Quelldatensatz
uspto-grants-1997_08
Patentnummer
US05658930

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