Dimethyl Sulfoxide → (R)-3-(2-fluoropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one

HRID 57348Notes

Reaction equation

HRID 57348 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C@H:13]([O:15][CH3:16])[CH3:14])[CH2:11][O:10][C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1.[F-:18].[K+].CS(C)=O>O>[F:18][C:2]1[N:7]=[C:6]([N:8]2[C@@H:12]([C@H:13]([O:15][CH3:16])[CH3:14])[CH2:11][O:10][C:9]2=[O:17])[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 522689Potassium FluorideHCID 90415843(R)-3-(2-chloropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one

Product 1

HCID 90416779(R)-3-(2-fluoropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-oneYield 87.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

To a microwe vial with stir bar was added (R)-3-(2-chloropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one (145 mg, 0.56 mmol), potassium fluoride (327 mg, 5.63 mmol) and DMSO (4 mL). Vial capped and heated to 120° C. in a sand bath for 3 hr. Reaction mixture was then cooled to room temperature, diluted with water and aqueous mixture extracted with EtOAc. The Organic phases were combined and washed with water, brine, dried (Na2SO4), filtered and concentrated to afford a white crystalline of (R)-3-(2-fluoropyrimidin-4-yl)-4-((R)-1-methoxyethyl)oxazolidin-2-one (117 mg, 0.49 mmol, 86% yield). LCMS m/z 242.1 (M+H)+, Rt 0.63 min.

Workup

  1. customVial capped
  2. customReaction mixture
  3. temperaturewas then cooled to room temperature
  4. extractionextracted with EtOAc
  5. washwashed with water, brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-6258fd54faf349dea27c33630c073763
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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