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Sodium ethoxide → tert-Butyl 4-(trifluoromethyl)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylate

HRID 1360165
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1360165
[O-]CC.[Na+].Cl.[CH:6]([NH2:8])=[NH:7].[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][CH:19]([C:22](=O)[C:23]([F:26])([F:25])[F:24])[C:18](=O)[CH2:17]1)=[O:15])([CH3:12])([CH3:11])[CH3:10]>C(O)C>[C:9]([O:13][C:14]([N:16]1[CH2:21][CH2:20][C:19]2[C:22]([C:23]([F:26])([F:24])[F:25])=[N:8][CH:6]=[N:7][C:18]=2[CH2:17]1)=[O:15])([CH3:12])([CH3:10])[CH3:11]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 2723922Sodium ethoxideHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 18456551tert-Butyl 3-oxo-4-(2,2,2-trifluoroacetyl)piperidine-1-carboxylate

Produkt 1

HCID 71630760tert-Butyl 4-(trifluoromethyl)-5,6-dihydropyrido[3,4-d]pyrimidine-7(8H)-carboxylateAusbeute 13 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702
Ethanol
Lösungsmittel
2×

Versuchsvorschrift

0.52 mL of sodium ethoxide (21% wt. ethanol solution) was added at room temperature to a solution in which 95 mg (1.18 mmol) of formamidine hydrochloric acid salt was dissolved in 2 mL of anhydrous ethanol at room temperature. After stirring at room temperature for 10 minutes, to the resulting solution, was added a solution in which 232 mg (0.786 mmol) of tert-butyl-3-oxo-4-(trifluoroacetyl)-piperidine-1-carboxylate (product of PREPARATION 47) was diluted with 2 mL of anhydrous ethanol. Thereafter, the temperature of the solution was raised to 80° C., followed by stirring for about 18 hours. After cooling to room temperature, ethanol was removed under reduced pressure, and the reaction solution was diluted with ethylacetate, then washed in sequence aqueous NaCl. An organic layer was dried over anhydrous magnesium sulfate and filtered off. The filtrated solution was distilled off under reduced pressure and then, the residue was isolated and purified by prep-TLC (ethylacetate 20% normal hexane in solvent) to give 30 mg of the title compound in a yield of 13%

Aufarbeitung

  1. temperatureThereafter, the temperature of the solution was raised to 80° C.
  2. stirringby stirring for about 18 hours
  3. temperatureAfter cooling to room temperature
  4. customethanol was removed under reduced pressure
  5. additionthe reaction solution was diluted with ethylacetate
  6. washwashed in sequence aqueous NaCl
  7. dry with materialAn organic layer was dried over anhydrous magnesium sulfate
  8. filtrationfiltered off
  9. distillationThe filtrated solution was distilled off under reduced pressure
  10. customthe residue was isolated
  11. custompurified by prep-TLC (ethylacetate 20% normal hexane in solvent)

Quellen und Nachweise

ORD-Eintrag
ord-51e4ba50899046288ceaf30c22df626a
Quelldatensatz
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07879848B2

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