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 1791137Notes

Reaction equation

HRID 1791137 reaction equation
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

Participants

8

Reactant 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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalystHCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
120 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-d2089d2c66814fd7a72fe951028b76be
Source dataset
uspto-grants-2006_07
Patent number
US07074787B2

Reaction notes

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