1,8-Diazabicyclo(5.4.0)undec-7-ene → 8-Ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

HRID 2300056Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2300056
[CH2:1]([NH:3][C:4]1[C:9]([CH:10]=[CH:11][C:12](OCC)=[O:13])=[CH:8][N:7]=[C:6]([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:5]=1)[CH3:2].N12CCCN=C1CCCCC2>C(N(CC)CC)C>[CH2:1]([N:3]1[C:4]2[N:5]=[C:6]([NH:17][C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[N:7]=[CH:8][C:9]=2[CH:10]=[CH:11][C:12]1=[O:13])[CH3:2]

Komponenten

4

Edukt 2

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 54014983Ethyl 3-(4-ethylamino-2-phenylamino pyrimidin-5-yl)acrylate

Produkt 1

HCID 53301998-Ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To a room temperature solution of ethyl 3-(4-ethylamino-2-phenylamino pyrimidin-5-yl)acrylate (179 mg, 0.57mmol) in 10 mL of triethylamine was added 90 μL of 1,8-diazabicyclo[5.4.0]undec-7-ene. The reaction mixture was heated at reflux for 8.5 hours then stirred at room temperature overnight. An additional amount of 1,8-diazabicyclo[5.4.0]undec-7-ene (90 μL) was added, and the reaction mixture was heated at reflux for 9 hours then stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and purified by flash chromatography, followed by recrystallization from ethyl acetate:hexane, to provide 8-ethyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 203-204° C.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 8.5 hours
  3. temperaturethe reaction mixture was heated
  4. temperatureat reflux for 9 hours
  5. stirringthen stirred at room temperature overnight
  6. concentrationThe reaction mixture was concentrated in vacuo
  7. custompurified by flash chromatography
  8. customfollowed by recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-17425cb1dc1f4184b3d29ac750b3a519
Quelldatensatz
uspto-grants-2002_12
Patentnummer
US06498163B1

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