Hydrochloric Acid → Diethyl pyrimidine-2,4-dicarboxylate

HRID 2384095Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2384095
N(OC(C)(C)C)=O.N[C:9]1[N:14]=[C:13]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:12]=[C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:10]=1.Cl>CN(C=O)C>[N:14]1[CH:9]=[CH:10][C:11]([C:20]([O:22][CH2:23][CH3:24])=[O:21])=[N:12][C:13]=1[C:15]([O:17][CH2:18][CH3:19])=[O:16]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 10857553Diethyl 6-aminopyrimidine-2,4-dicarboxylate

Produkt 1

HCID 66701935Diethyl pyrimidine-2,4-dicarboxylate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

Next, To a stirred solution of tert-butyl nitrite (268 mg, 2.34 mmol.) in DMF (5 mL) at 60° C. is added a solution of diethyl 6-aminopyrimidine-2,4-dicarboxylate (280 mg, 1.17 mmol) in DMF (0.5 mL) dropwise and mixture is heated at 60° C. for 18 hours. The mixture is cooled to room temperature and poured into 1N HCl (10 mL). The mixture is extracted three times with ethyl acetate and the combined organic layers are washed with water and brine then is dried over magnesium sulfate. The solvent is removed under reduced pressure and the residue is purified by flash chromatography (heptane/ethyl acetate=4:1) to give diethyl pyrimidine-2,4-dicarboxylate.

Aufarbeitung

  1. temperatureThe mixture is cooled to room temperature
  2. extractionThe mixture is extracted three times with ethyl acetate
  3. washthe combined organic layers are washed with water and brine
  4. dry with materialthen is dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure
  6. customthe residue is purified by flash chromatography (heptane/ethyl acetate=4:1)

Quellen und Nachweise

ORD-Eintrag
ord-e6731a0cf6c5432e82b047f087460ca0
Quelldatensatz
uspto-grants-2012_09
Patentnummer
US08263629B2

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