Thiophenol → 2-Fluoro-4-(2-(phenylamino)pyrimidin-5-yl)phenol

HRID 1993354Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1993354
[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:14][CH:15]=2)[CH:5]=[CH:6][C:7]=1[O:8]C.C1(S)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>CN1C(=O)CCC1.O>[F:1][C:2]1[CH:3]=[C:4]([C:10]2[CH:15]=[N:14][C:13]([NH:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[N:12][CH:11]=2)[CH:5]=[CH:6][C:7]=1[OH:8]

Komponenten

6

Edukt 3

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 574453935-(3-fluoro-4-methoxyphenyl)-N-phenylpyrimidin-2-amine

Produkt 1

HCID 574453942-Fluoro-4-(2-(phenylamino)pyrimidin-5-yl)phenol

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 5-(3-fluoro-4-methoxyphenyl)-N-phenylpyrimidin-2-amine (Step 2, 0.066 g, 0.22 mmol), thiophenol (0.20 g, 1.0 mmol), and K2CO3 (0.15 g, 1.1 mmol) in NMP (2 mL) was heated at 120° C. for 20 h. The mixture was cooled to RT and diluted with H2O (4 mL). After stirring for 10 min, the resulting suspension was filtered, and the solid was further washed with H2O. The solid was washed with hexanes to provide the title compound as a brown solid. MS (ESI pos. ion) m/z: 282. Calc'd for C16H12FN3O: 281.10.

Aufarbeitung

  1. temperatureThe mixture was cooled to RT
  2. filtrationthe resulting suspension was filtered
  3. washthe solid was further washed with H2O
  4. washThe solid was washed with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-b925e905939943bda3fa52233e6c9381
Quelldatensatz
uspto-grants-2010_01
Patentnummer
US07652009B2

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