Acetic Acid → 6-(4-Fluorophenyl)pyrido[3,2-d]pyrimidin-4(1H)-one

HRID 1517437Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1517437
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:6]=[CH:7][NH:8][C:9](=[O:12])[C:10]=2[N:11]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+].C(O)(=O)C>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]=[CH:7][NH:8][C:9](=[O:12])[C:10]=3[N:11]=2)=[CH:16][CH:15]=1

Komponenten

8

Edukt 4

HCID 176Acetic AcidHCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 1354270966-Chloropyrido[3,2-d]pyrimidin-4(3H)-one

Produkt 1

HCID 1360008906-(4-Fluorophenyl)pyrido[3,2-d]pyrimidin-4(1H)-oneAusbeute 90,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

To a solution of 6-chloro-pyrido[3,2-d]pyrimidin-4(3H)one (1.0 g, 5.5 mmol) in dioxane (80 ml) and water (20 ml) was added 4-fluorophenylboronic acid (770 mg, 5.5 mmol), K2CO3 (2.28 g, 16.5 mmol), and tetrakis(triphenylphosphine)palladium(0) (290 mg, 0.25 mmol). The mixture was heated at reflux for 20 hours. After cooling to room temperature, the reaction mixture was neutralized to pH 5-6 with acetic acid, concentrated to a small volume, filtered and washed with water to yield a crude product. The crude residue was purified by silica gel flash chromatography, the mobile phase being a mixture of methanol and dichloromethane, in a volume ratio of 1:30, yielding the title compound as a white solid (1.2 g, yield: 90%) which was characterised by its mass spectrum as follows: MS (m/z): 242 ([M+H]+, 100).

Aufarbeitung

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 20 hours
  3. concentrationconcentrated to a small volume
  4. filtrationfiltered
  5. washwashed with water
  6. customto yield a crude product
  7. customThe crude residue was purified by silica gel flash chromatography
  8. additiona mixture of methanol and dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-4b5a421e92324505a837009abfae4496
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232278B2

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