1-(3,4-dichlorophenyl)ethanamine → (R)-3-(2-((R)-1-(3,4-dichlorophenyl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one

HRID 1850201Notes

Reaction equation

HRID 1850201 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:11][O:10][C:9]2=[O:19])[CH:5]=[CH:4][N:3]=1.[Cl:20][C:21]1[CH:22]=[C:23]([CH:28]([NH2:30])[CH3:29])[CH:24]=[CH:25][C:26]=1[Cl:27]>CS(C)=O.CCOC(C)=O>[Cl:20][C:21]1[CH:22]=[C:23]([C@H:28]([NH:30][C:2]2[N:7]=[C:6]([N:8]3[C@H:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:11][O:10][C:9]3=[O:19])[CH:5]=[CH:4][N:3]=2)[CH3:29])[CH:24]=[CH:25][C:26]=1[Cl:27].[Cl:20][C:21]1[CH:22]=[C:23]([C@@H:28]([NH:30][C:2]2[N:7]=[C:6]([N:8]3[C@H:12]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH2:11][O:10][C:9]3=[O:19])[CH:5]=[CH:4][N:3]=2)[CH3:29])[CH:24]=[CH:25][C:26]=1[Cl:27]

Participants

6

Reactant 2

HCID 31592421-(3,4-dichlorophenyl)ethanamineHCID 86730136(R)-3-(2-chloropyrimidin-4-yl)-4-phenyloxazolidin-2-one

Product 2

HCID 86730242(R)-3-(2-((R)-1-(3,4-dichlorophenyl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-oneHCID 86730243(R)-3-(2-((S)-1-(3,4-dichlorophenyl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of (R)-3-(2-chloropyrimidin-4-yl)-4-phenyloxazolidin-2-one (83 mg, 0.30 mmol) and 1-(3,4-dichlorophenyl)ethanamine (260 mg, 1.37 mmol, 4.5 equiv) in DMSO (1.5 mL) was heated at 110° C. for 1½ h. The reaction mixture was diluted with EtOAc (8 mL) and washed with water (30 mL). After separation, the aqueous phase was extracted with EtOAc (3×8 mL). Combined organics were dried over Na2SO4, filtered and concentrated. Silica gel column chromatography (EtOAc/Heptane 0 to 40%) provided (R)-3-(2-((R)-1-(3,4-dichlorophenyl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one and (R)-3-(2-((S)-1-(3,4-dichlorophenyl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one.

Workup

  1. washwashed with water (30 mL)
  2. customAfter separation
  3. extractionthe aqueous phase was extracted with EtOAc (3×8 mL)
  4. dry with materialCombined organics were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-af4e7644a60a4be6a0918dcf82d5e5cb
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

Loading…