Sodium Thiosulfate → HCID 70982746, compound

HRID 2280720Notes

Reaction equation

HRID 2280720 reaction equation
[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]2[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=[C:12](SC)[N:11]=2)[CH2:4]1.[CH:21]1C=C(Cl)C=C(C(OO)=O)C=1.[S:32]([O-:36])([O-])(=[O:34])=S.[Na+].[Na+]>C(Cl)Cl.CC(C)=O>[CH3:1][O:2][C@H:3]1[CH2:8][CH2:7][CH2:6][C@@H:5]([NH:9][C:10]2[C:15]([C:16]([NH2:18])=[O:17])=[CH:14][N:13]=[C:12]([S:32]([CH3:21])(=[O:36])=[O:34])[N:11]=2)[CH2:4]1

Participants

6

Reactant 3

HCID 24477Sodium ThiosulfateHCID 70297m-Chloroperbenzoic acidHCID 71237304HCID 71237304, compound

Product 1

HCID 70982746HCID 70982746, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-((1R,3S)-3-methoxycyclohexylamino)-2-(methylthio)pyrimidine-5-carboxamide (1.1081 g, 3.74 mmol) in DCM (18.69 mL) and acetone (18.69 mL) at room temperature was added mCPBA (1.676 g, 7.48 mmol) in five batches over 2 min and stirred at room temperature for 16 h. To the crude reaction mixture was added 10% aqueous sodium thiosulfate solution (35 mL) and the mixture was stirred for 5 min before evaporation of the volatile solvents. The material was partitioned between ethyl acetate and water, and the organic layer was then washed with saturated aqueous sodium bicarbonate solution and then brine. The combined aqueous layers were then washed with ethyl acetate (3×), organic layers were combined, dried over sodium sulfate, filtered, and condensed. After drying under high vacuum, 4-((1R,3S)-3-methoxy-cyclohexylamino)-2-(methylsulfonyl)pyrimidine-5-carboxamide (0.9887 g, 3.01 mmol, 81% yield) was obtained as a white solid. MS (ESI) m/z 329.3 [M+1]+.

Workup

  1. customTo the crude reaction mixture
  2. stirringthe mixture was stirred for 5 min before evaporation of the volatile solvents
  3. customThe material was partitioned between ethyl acetate and water
  4. washthe organic layer was then washed with saturated aqueous sodium bicarbonate solution
  5. washThe combined aqueous layers were then washed with ethyl acetate (3×), organic layers
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customcondensed
  9. customAfter drying under high vacuum

Sources & evidence

ORD record
ord-0c9eb2e5b0b14fcc9b5325c52dbc0dfe
Source dataset
uspto-grants-2015_09
Patent number
US09139534B2

Reaction notes

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