Cesium carbonate → HCID 59485787, compound

HRID 1972257Notes

Reaction equation

HRID 1972257 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[CH:14]=3)[CH2:11][O:10][C:9]2=[O:20])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Cl[C:28]1[N:33]=[CH:32][CH:31]=[CH:30][N:29]=1>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C@@H:12]([C:13]3[CH:18]=[CH:17][CH:16]=[C:15]([O:19][C:28]4[N:33]=[CH:32][CH:31]=[CH:30][N:29]=4)[CH:14]=3)[CH2:11][O:10][C:9]2=[O:20])=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 744042-ChloropyrimidineHCID 59485707HCID 59485707, compound

Product 1

HCID 59485787HCID 59485787, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

To (S)-3-(4-chlorophenyl)-4-(3-hydroxyphenyl)oxazolidin-2-one (0.05 mmol) is added Cs2CO3 (0.1 mmol) and 2-chloropyrimidine (0.06 mmol) in DMF (1 mL). The mixture is stirred at 80° C. for 3 h then cooled to room temperature and filtered through Whatman 0.42 μM filter and purified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA)). HPLC-MS calculated for C19H14ClN3O3 (M+H+): 368.0, found 368.0.

Workup

  1. temperaturethen cooled to room temperature
  2. filtrationfiltered through Whatman 0.42 μM
  3. filtrationfilter
  4. custompurified by preparative HPLC (C-18, 10-90% ACN/water (0.05% TFA))

Sources & evidence

ORD record
ord-3c99b104117c4c5087c509202750cdd1
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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