Sodium Bicarbonate → N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[[(1R,2R)-2,3-dihydroxy-1-methylpropyl]oxy]-4-pyrimidinyl]-methanesulfonamide

HRID 1024907Notes

Reaction equation

HRID 1024907 reaction equation
[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:20])=[O:19])[CH:14]=[C:13]([O:22][C@@H:23]([C@H:25]2[CH2:29][O:28]C(C)(C)[O:26]2)[CH3:24])[N:12]=1.C(=O)(O)[O-].[Na+]>C(Cl)Cl.O.O.O.O.O.O.[Fe](Cl)(Cl)Cl>[F:1][C:2]1[C:7]([F:8])=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:9][S:10][C:11]1[N:16]=[C:15]([NH:17][S:18]([CH3:21])(=[O:19])=[O:20])[CH:14]=[C:13]([O:22][C@H:23]([CH3:24])[C@H:25]([OH:26])[CH2:29][OH:28])[N:12]=1

Participants

5

Reactant 2

HCID 516892Sodium BicarbonateHCID 67051274N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy)-4-pyrimidinyl]-methanesulfonamide

Product 1

HCID 11568270N-[2-[[(2,3-Difluorophenyl)methyl]thio]-6-[[(1R,2R)-2,3-dihydroxy-1-methylpropyl]oxy]-4-pyrimidinyl]-methanesulfonamide

Reagents, catalysts & solvents 2

HCID 16211236Trichloroiron;hexahydrateCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-[[(2,3-difluorophenyl)methyl]thio]-6-[(1R)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]ethoxy]-4-pyrimidinyl]-methanesulfonamide (the product of step i) (0.23 g) in DCM (5 mL) was added iron (III) chloride hexahydrate (0.25 g). The reaction mixture was stirred at ambient temperature for 2 h then saturated aqueous sodium bicarbonate (2 mL) was added. The layers were separated and the aqueous material extracted with DCM (×3) and ethyl acetate (×3). The combined organic extracts were washed with brine, dried (MgSO4), filtered and evaporated. The residual yellow solid was precipitated from 10% DCM in Et2O, filtered and the resulting material washed with minimal Et2O (2×1 mL) to afford the title compound as a white powder. Yield: 24 mg.

Workup

  1. customThe layers were separated
  2. extractionthe aqueous material extracted with DCM (×3) and ethyl acetate (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual yellow solid was precipitated from 10% DCM in Et2O
  8. filtrationfiltered
  9. washthe resulting material washed with minimal Et2O (2×1 mL)

Sources & evidence

ORD record
ord-441068fc31674834a40b4d7c98ea6724
Source dataset
uspto-grants-2014_05
Patent number
US08722883B2

Reaction notes

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