1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → 3-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-methyl-oxazolidin-2-one

HRID 1791137

Reaktionsgleichung

Reaktionsgleichung von HRID 1791137
CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.[Cl:43][C:44]1[CH:45]=[C:46]([NH:50][C:51]2[N:56]=[C:55]([C:57]3[CH:62]=[CH:61][N:60]=[C:59](Cl)[CH:58]=3)[CH:54]=[CH:53][N:52]=2)[CH:47]=[CH:48][CH:49]=1.[CH3:64][C@@H:65]1[CH2:69][O:68][C:67](=[O:70])[NH:66]1.CC([O-])(C)C.[Na+]>C1(C)C=CC=CC=1.C(OCC)(=O)C.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Cl:43][C:44]1[CH:45]=[C:46]([NH:50][C:51]2[N:56]=[C:55]([C:57]3[CH:62]=[CH:61][N:60]=[C:59]([N:66]4[CH:65]([CH3:64])[CH2:69][O:68][C:67]4=[O:70])[CH:58]=3)[CH:54]=[CH:53][N:52]=2)[CH:47]=[CH:48][CH:49]=1

Komponenten

8

Edukt 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 2734858(R)-4-Methyloxazolidin-2-oneHCID 9905031N-(3-chlorophenyl)-4-(2-chloropyridin-4-yl)pyrimidin-2-amineHCID 23676156Sodium t-butoxide

Produkt 1

HCID 220278603-{4-[2-(3-Chloro-phenylamino)-pyrimidin-4-yl]-pyridin-2-yl}-4-methyl-oxazolidin-2-one

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A solution of Xantphos (0.018 g) and Pd2(dba)3 (0.014 g) in toluene (2 ml) is stirred under argon at room temperature for 20 minutes. Then (3-chloro-phenyl)-[4-(2-chloro-pyridin-4-yl)-pyrimidin-2-yl]-amine (0.20 g), (R)-4-methyl-oxazolidin-2-one (0.127 g), NaOtBu (0.085 g) and toluene ((2 ml) are added. The reaction mixture is refluxed at 120° C. for 1 hour. After this time the mixture is cooled to room temperature, diluted with ethyl acetate, and washed with water. The organic layer is dried over Na2SO4 and concentrated under vacuum. The residue is purified by silicagel chromatography to give the title compound, m.p. 177–178° C. and [α]D=−72.0° (20° C., c=1).

Aufarbeitung

  1. temperatureAfter this time the mixture is cooled to room temperature
  2. washwashed with water
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated under vacuum
  5. customThe residue is purified by silicagel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-d2089d2c66814fd7a72fe951028b76be
Quelldatensatz
uspto-grants-2006_07
Patentnummer
US07074787B2

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