Reaktionsgleichung
O[C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:3]=1.P(Cl)(Cl)([Cl:28])=O>>[Cl:28][C:2]1[N:7]([CH3:8])[C:6](=[O:9])[C:5]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[CH:11]=2)=[C:4]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)[N:3]=1Komponenten
3
Reaktionsbedingungen
- Temperatur
- 105 °C
Versuchsvorschrift
A suspension of 2-hydroxy-3-methyl-5-naphthalen-2-yl-6-pyridin-4-yl-3H-pyrimidin-4-one (10.0 g, 30.4 mmol) and phosphorous oxychloride (250 mL, 3 mol) was heated to 105° C. for 6 h to form a solution. Monitoring reaction by HPLC showed ˜90% conversion. The reaction solution was cooled and the solvent removed under reduced pressure. Foam residue was dissolved in 500 mL 5% ethanol/chloroform. The organic layer was washed with 100 mL water three times and once with 100 mL 5% NaHCO3. Organic dried over magnesium sulfate, then dried onto 30 g of silica. Final product purified on 400 g silica eluting with 0 to 2.5% methanol/dichloromethane to give a yellow solid. M+1=348.
Aufarbeitung
- customto form a solution
- customMonitoring reaction by HPLC
- temperatureThe reaction solution was cooled
- customthe solvent removed under reduced pressure
- dissolutionFoam residue was dissolved in 500 mL 5% ethanol/chloroform
- washThe organic layer was washed with 100 mL water three times and once with 100 mL 5% NaHCO3
- dry with materialOrganic dried over magnesium sulfate
- customdried onto 30 g of silica
- customFinal product purified on 400 g silica eluting with 0 to 2.5% methanol/dichloromethane
- customto give a yellow solid
Quellen und Nachweise
- ORD-Eintrag
- ord-5a48cb219acb4ecd8926f656b8e47788
- Quelldatensatz
- uspto-grants-2008_09
- Patentnummer
- US07429594B2
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