Ethyl ethoxyacetate → 2-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4ahpyrido[2,3-d]pyrimidin-7-one

HRID 459906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 459906
[NH2:1][CH:2]1[CH:7]([CH:8]=O)[CH:6]=[N:5][C:4]([S:10][CH2:11][CH2:12][CH2:13][CH3:14])=[N:3]1.[CH2:15]([O:17][CH2:18][C:19](OCC)=[O:20])[CH3:16].CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH2:11]([S:10][C:4]1[N:5]=[CH:6][CH:7]2[CH:8]=[C:18]([O:17][CH2:15][CH3:16])[C:19](=[O:20])[NH:1][CH:2]2[N:3]=1)[CH2:12][CH2:13][CH3:14]

Komponenten

5

Edukt 3

HCID 69955Ethyl ethoxyacetate2×HCID 21956055HCID 21956055, VerbindungHCID 23665647Potassium tert-butoxide

Produkt 1

HCID 219560512-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4ahpyrido[2,3-d]pyrimidin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

4-Amino-2-butylsulfanyl-4,5-dihydro-pyrimidine-5-carbaldehyde (3 g, 14.2 mmol, furnished by scaleup) and ethyl ethoxyacetate (2.34 g, 2.4 ml, 17.75 mmol) were stirred in 80 ml toluene at 0°-5° C. under nitrogen. Potassium t-butoxide (1.75 g, 15.6 mmol) was added gradually. The mixture was stirred to ambient temperature, and then to 65° C. for 48 hours. An additional 20 ml of toluene and 2.4 ml ethyl ethoxyacetate were added and the reaction was maintained at 65° C. over the weekend. The reaction mixture was concentrated in vacuo and triturated with EtOAc to remove the remaining starting aldehyde. The remaining solid was further triturated with chloroform to remove additional impurities. 3.66 g of 2-Butylsulfanyl-6-ethoxy-8,8a-dihydro-4aHpyrido[2,3-d]pyrimidin-7-one (1A) of a purity greater than 80% as judged by MS/HPLC and NMR was collected.

Aufarbeitung

  1. temperaturethe reaction was maintained at 65° C. over the weekend
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customtriturated with EtOAc
  4. customto remove the remaining starting aldehyde
  5. customThe remaining solid was further triturated with chloroform
  6. customto remove additional impurities
  7. customwas collected

Quellen und Nachweise

ORD-Eintrag
ord-6cd10b64cb5b47d8a8a9f9930b4e7750
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196097B2

Notizen zur Reaktion

Wird geladen…