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ノート

反応式

HRID 1791137 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9811564Bis(dibenzylideneacetone)palladium触媒HCID 1140Toluene溶媒2 回HCID 8857Ethyl Acetate溶媒

反応条件

温度
120 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d2089d2c66814fd7a72fe951028b76be
出典データセット
uspto-grants-2006_07
特許番号
US07074787B2

反応ノート

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