Pyridine → (3-Chloro-4-fluoro-phenyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

HRID 133022Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 133022
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25]O)=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8].N1C=CC=CC=1.S(Cl)([Cl:35])=O>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[C:11]3[CH:18]=[C:17]([C:19]4[CH:24]=[CH:23][C:22]([CH2:25][Cl:35])=[CH:21][CH:20]=4)[NH:16][C:12]=3[N:13]=[CH:14][N:15]=2)[CH:5]=[CH:6][C:7]=1[F:8]

Komponenten

5

Edukt 3

HCID 1049Pyridine2×HCID 24386Thionyl Chloride2×HCID 11234001{4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol

Produkt 1

HCID 11383626(3-Chloro-4-fluoro-phenyl)-[6-(4-chloromethyl-phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-yl]-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

184 mg (0.5 mmol) {4-[4-(3-Chloro-4-fluoro-phenylamino)-7H-pyrrolo[2,3-d]pyrimidin-6-yl]-phenyl}-methanol are suspended in 15 ml toluene. Pyridine (44 μl, 0.55 mmol) and thionyl chloride (40 μl, 0.55 mmol) are added and the mixture is stirred at RT for 16 h. A second portion of the same amounts of pyridine and thionyl chloride are then added and the mixture stirred for 1 additional hour. The solvent is evaporated and the residue suspended in water containing a small amount of sodium bicarbonate (pH˜8). After filtration, the product was thoroughly washed with water and ether and dried to give crude title compound; m.p.>300° C.; Rf (dichloromethane/ethanol 95:5 plus 1% conc. ammonia)=0.42; HPLC tR=11.33 min.

Aufarbeitung

  1. stirringthe mixture stirred for 1 additional hour
  2. customThe solvent is evaporated
  3. filtrationAfter filtration
  4. washthe product was thoroughly washed with water and ether
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-64bff5299e9d43f68021ec0a03f097a7
Quelldatensatz
uspto-grants-2008_06
Patentnummer
US07390805B2

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