Diisopropylethylamine → (R)-3-(2-((R)-1-(biphenyl-4-yl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one

HRID 1850199Notes

Reaction equation

HRID 1850199 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.[C:21]1([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH:26]=[CH:25][C:24]([CH:27]([NH2:29])[CH3:28])=[CH:23][CH:22]=1.CCN(C(C)C)C(C)C>CS(C)=O.CCOC(C)=O>[C:21]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:22]=[CH:23][C:24]([C@H:27]([NH:29][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)[CH3:28])=[CH:25][CH:26]=1.[C:21]1([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:22]=[CH:23][C:24]([C@@H:27]([NH:29][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)[CH3:28])=[CH:25][CH:26]=1

Participants

7

Reactant 3

HCID 81531DiisopropylethylamineHCID 13012106HCID 13012106, compoundHCID 86730136(R)-3-(2-chloropyrimidin-4-yl)-4-phenyloxazolidin-2-one

Product 2

HCID 86730237(R)-3-(2-((R)-1-(biphenyl-4-yl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-oneHCID 86730238(R)-3-(2-((S)-1-(biphenyl-4-yl)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 (97 mg, 0.35 mmol), 1-(biphenyl-4-yl)ethanamine hydrochloride (304 mg, 1.30 mmol, 3.7 equiv) and iPr2NEt (0.307 mL, 1.76 mmol, 5.0 equiv) in DMSO (1 mL) was heated at 110° C. for 1½ h and at 130° C. for 20 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 10 to 50%) provided (R)-3-(2-((R)-1-(biphenyl-4-yl)ethylamino)pyrimidin-4-yl)-4-phenyloxazolidin-2-one and (R)-3-(2-((S)-1-(biphenyl-4-yl)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-b01fb4f07d6346cda56f4acf5e1e728d
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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