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 1791137노트

반응식

HRID 1791137 반응식
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

참가 물질

8

반응물 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

생성물 1

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

시약·촉매·용매 3

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 1140Toluene용매2회HCID 8857Ethyl Acetate용매

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온도
120 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-d2089d2c66814fd7a72fe951028b76be
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07074787B2

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