Isobutylamine → 8-isobutyl-6-(4-methoxy-phenyl)-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidine-7-one

HRID 11795

Reaktionsgleichung

Reaktionsgleichung von HRID 11795
C[O:2][C:3](=O)[CH:4]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[CH2:5][C:6]1[C:7](Cl)=[N:8][C:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:10][CH:11]=1.[CH2:29]([NH2:33])[CH:30]([CH3:32])[CH3:31]>>[CH2:29]([N:33]1[C:7]2[N:8]=[C:9]([NH:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:10]=[CH:11][C:6]=2[CH2:5][CH:4]([C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C:3]1=[O:2])[CH:30]([CH3:32])[CH3:31]

Komponenten

3

Edukt 2

HCID 6558IsobutylamineHCID 210443143-(4-Chloro-2-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester

Produkt 1

HCID 103863918-isobutyl-6-(4-methoxy-phenyl)-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidine-7-one

Versuchsvorschrift

A mixture of 3-(4-chloro-2-phenylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester (40 mg, 0.1 mmol) (from Example 12a supra) and isobutylamine (2.0 mL) (Aldrich) was heated at reflux for 3 hours. The reaction mixture was concentrated in vacuo and purified by preparative thin layer chromatography to give 8-isobutyl-6-(4-methoxy-phenyl)-2-phenylamino-5,8-dihydro-6H-pyrido[2,3-d]pyrimidine-7-one; (Yield 4.6 mg, 11.4%); and 3-(2-phenylamino-4-isobutylamino-pyrimidin-5-yl)-2-(4-methoxy-phenyl)-propionic acid methyl ester. (Yield 18.2 mg, 41.9%).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated in vacuo
  4. custompurified by preparative thin layer chromatography

Quellen und Nachweise

ORD-Eintrag
ord-16c01f2bbc1b441a947666da49a93695
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07098332B2

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