Methanol → (S)-2-chloro-N-(3,3-dimethyl-1-(methylsulfonyl)butan-2-yl)-5-fluoropyrimidin-4-amine

HRID 1055071Notes

Reaction equation

HRID 1055071 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:13]([CH3:16])([CH3:15])[CH3:14])[CH2:10]SC)[C:5]([F:17])=[CH:4][N:3]=1.O[O:19][S:20]([O-:22])=O.[K+].[CH3:24]O>O>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][C@@H:9]([C:13]([CH3:14])([CH3:16])[CH3:15])[CH2:10][S:20]([CH3:24])(=[O:22])=[O:19])[C:5]([F:17])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 86714753(S)-2-chloro-N-(3,3-dimethyl-1-(methylthio)butan-2-yl)-5-fluoropyrimidin-4-amine2×

Product 1

HCID 86714754(S)-2-chloro-N-(3,3-dimethyl-1-(methylsulfonyl)butan-2-yl)-5-fluoropyrimidin-4-amine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a cold (0° C.) solution of (S)-2-chloro-N-(3,3-dimethyl-1-(methylthio)butan-2-yl)-5-fluoropyrimidin-4-amine, 78a, (0.15 g, 0.54 mmol) in methanol (10 mL) was added Oxone (0.50 g, 0.81 mmol). The solution was stirred at room temperature for 3 hours. The solution was concentrated in vacuo to give a white residue which was dissolved in water (10 mL). The aqueous layer was extracted with EtOAc (3×10 mL). The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo to afford 150 mg of the desired product as a white solid: LC/MS (60-90% ACN/water 5 min with 0.9% FA) m/z 310.31 (M+H) RT=2.60 minutes.

Workup

  1. concentrationThe solution was concentrated in vacuo
  2. customto give a white residue which
  3. extractionThe aqueous layer was extracted with EtOAc (3×10 mL)
  4. dry with materialThe combined organic phases were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f806cf6aba2c4d0e9c4c051173bf9807
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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