2-Iodobutane → 8-sec-Butyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one
Reaktionsgleichung
[H-].[Na+].[C:3]1([NH:9][C:10]2[N:11]=[CH:12][C:13]3[CH:19]=[CH:18][C:17](=[O:20])[NH:16][C:14]=3[N:15]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.I[CH:22]([CH2:24][CH3:25])[CH3:23]>CN(C)C=O>[CH:22]([N:16]1[C:14]2[N:15]=[C:10]([NH:9][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=3)[N:11]=[CH:12][C:13]=2[CH:19]=[CH:18][C:17]1=[O:20])([CH2:24][CH3:25])[CH3:23]Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 50 °C
Versuchsvorschrift
To a suspension of NaH (47 mg of a 60% suspension of NaH in mineral oil) in 6 mL of dimethylformamide was added 2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one (202 mg, 0.85 mmol). The reaction mixture was heated to 50° C. to 60° C. resulting in a yellow solution. The solution was cooled slightly, and 2-iodobutane (140 μL, 1.22 mmol) was added. The reaction was heated at 50° C. for 20 minutes, then cooled to room temperature and partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated in vacuo. Purification by flash chromatography eluting with 2:1 ethyl acetate:hexane gave 29 mg (12%) of 8-sec-butyl-2-phenylamino-8H-pyrido[2,3-d]pyrimidin-7-one, mp 155-156° C.
Aufarbeitung
- temperatureThe reaction mixture was heated to 50° C. to 60° C.
- customresulting in a yellow solution
- temperatureThe solution was cooled slightly
- temperaturecooled to room temperature
- custompartitioned between water and ethyl acetate
- dry with materialThe organic layer was dried over magnesium sulfate
- filtrationfiltered
- concentrationconcentrated in vacuo
- customPurification by flash chromatography
- washeluting with 2:1 ethyl acetate
Quellen und Nachweise
- ORD-Eintrag
- ord-f06ff9445277496eade8ac29d9c4c1cd
- Quelldatensatz
- uspto-grants-2002_12
- Patentnummer
- US06498163B1
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