Sodium Bicarbonate → HCID 58504543, compound

HRID 2367610Notes

Reaction equation

HRID 2367610 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([F:16])([F:15])[F:14])[N:5]=[C:4](SC)[N:3]=1.O[O:20][S:21]([O-:23])=O.[K+].[C:25]([O-])(O)=O.[Na+]>CO.O>[Cl:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][CH2:10][C@H:9]2[C:13]([F:15])([F:16])[F:14])[N:5]=[C:4]([S:21]([CH3:25])(=[O:23])=[O:20])[N:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 23707502Potassium hydroxy sulfiteHCID 58504425HCID 58504425, compound

Product 1

HCID 58504543HCID 58504543, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

A suspension of 4-chloro-2-(methylthio)-6-[(2S)-2-(trifluoromethyl)-1-pyrrolidinyl]pyrimidine (1.45 g, 4.87 mmol) in CH3OH (15 mL) was cooled in an ice bath and treated slowly with a premixed solution of oxone (3.89 g, 6.33 mmol) in water (5 mL). The reaction was let stir at room temperature overnight. The reaction was diluted with water (20 mL) followed by saturated NaHCO3 (30 mL). The mixture was extracted with EtOAc (3×50 mL). The organic was combined, washed with saturated NaCl solution, dried over MgSO4, filtered and concentrated to afford the crude title compound (1.55 g) as a yellowish oil. LC-MS (ES) m/z=330 [M+H]+.

Workup

  1. temperaturewas cooled in an ice bath
  2. extractionThe mixture was extracted with EtOAc (3×50 mL)
  3. washwashed with saturated NaCl solution
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-397eb43b261c446c9075aff20a42ab11
Source dataset
uspto-grants-2014_04
Patent number
US08697685B2

Reaction notes

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