Phenylboronic Acid → 2-Amino-6-phenylpyrimidine-4-carboxylic acid
Reaktionsgleichung
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([O:10]C)=[O:9])[CH:5]=[C:4](Cl)[N:3]=1.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C([O-])(O)=O.[Na+]>C1COCC1>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([OH:10])=[O:9])[CH:5]=[C:4]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[N:3]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 90 °C
Versuchsvorschrift
A solution of methyl 2-amino-6-chloropyrimidine-4-carboxylate (0.2 g, 1.07 mmol) and phenylboronic acid (0.16 g, 1.3 mmol) in THF (10 mL) was treated with saturated aqueous NaHCO3 (1.6 mL). Nitrogen was bubbled through the solution for 5 min then tetrakis(triphenylphosphine)palladium(0) (0.04 g) was added and the mixture refluxed under nitrogen overnight. The mixture was treated with aqueous LiOH (1-M, 1 mL), heated at 90° C. for 2 h, concentrated in vacuo and partitioned between ethyl acetate and water. The aqueous layer was acidified to pH 1 with 2-N HCl, the resulting suspension centrifuged, the liquors decanted and the resulting solid dried to give the title compound (0.17 g, 72%) as a white powder which was used directly in the next step without further purification; M/Z 216 (M+H)+; retention time 1.60 min (Method AM).
Aufarbeitung
- customNitrogen was bubbled through the solution for 5 min
- additiontetrakis(triphenylphosphine)palladium(0) (0.04 g) was added
- temperaturethe mixture refluxed under nitrogen overnight
- additionThe mixture was treated with aqueous LiOH (1-M, 1 mL)
- concentrationconcentrated in vacuo
- custompartitioned between ethyl acetate and water
- customthe liquors decanted
- customthe resulting solid dried
Quellen und Nachweise
- ORD-Eintrag
- ord-bd6618b5cde74a8da7b403db0ef62d52
- Quelldatensatz
- uspto-grants-2011_01
- Patentnummer
- US07875600B2
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