Water → HCID 86730138, compound

HRID 1850109Notes

Reaction equation

HRID 1850109 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[C:9]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:19][O:18][C:17](=[O:20])[NH:16]2)=[CH:11][CH:10]=1.[H-].[Na+].O>CN(C=O)C.CCOC(C)=O.[Cl-].[Na+].O>[C:9]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:14]=[CH:13][C:12]([C@H:15]2[CH2:19][O:18][C:17](=[O:20])[N:16]2[C:6]2[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=2)=[CH:11][CH:10]=1

Participants

8

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 775312,4-DichloropyrimidineHCID 86730135HCID 86730135, compound

Product 1

HCID 86730138HCID 86730138, compoundYield 45.1%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×HCID 57417360Sodium chloride; waterSolvent2×

Procedure

To a solution of 2,4-dichloropyrimidine (46.5 mg, 0.312 mmol) and (S)-4-(biphenyl-4-yl)oxazolidin-2-one (74.7 mg, 0.312 mmol) in DMF (700 μL) was added NaH (60% wt., 10.49 mg, 0.437 mmol) in two portions within ˜5 min [Caution: exotherm; gas development] at room temperature (water bath). The reaction mixture was stirred for 1.5 hour. The mixture was diluted with EtOAc (25 mL), stirred for 5 min and then diluted slowly with diluted brine (10 mL; 1:1 brine/water). The mixture was poured into diluted brine (40 mL) and EtOAc (25 mL). The separated organic phase was washed with diluted brine (3×40 ml), dried over Na2SO4, filtered off and concentrated under reduced pressure. The residue was purified by column chromatography [SiO2, 40 g, EtOAc/heptane] to provide (S)-4-(biphenyl-4-yl)-3-(2-chloropyrimidin-4-yl)oxazolidin-2-one (49.5 mg). LCMS m/z 352.2 (M+H)+, Rt 1.06 min.

Workup

  1. stirringstirred for 5 min
  2. washThe separated organic phase was washed with diluted brine (3×40 ml)
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered off
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography [SiO2, 40 g, EtOAc/heptane]

Sources & evidence

ORD record
ord-ed3f86bd375849cc947d2c4ff163b12b
Source dataset
uspto-grants-2015_02
Patent number
US08957068B2

Reaction notes

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