Sodium Methoxide → (S)-2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutane-1-thiol

HRID 1055069Notes

Reaction equation

HRID 1055069 reaction equation
C(=O)([S:3][CH2:4][C@@H:5]([NH:10][C:11]1[C:16]([F:17])=[CH:15][N:14]=[C:13]([Cl:18])[N:12]=1)[C:6]([CH3:9])([CH3:8])[CH3:7])C.C[O-].[Na+]>CO>[Cl:18][C:13]1[N:12]=[C:11]([NH:10][C@@H:5]([C:6]([CH3:8])([CH3:7])[CH3:9])[CH2:4][SH:3])[C:16]([F:17])=[CH:15][N:14]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86714751(S)-S-2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutyl ethanethioate2×

Product 1

HCID 86714752(S)-2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutane-1-thiol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a nitrogen-purged solution of (S)—S-2-(2-chloro-5-fluoropyrimidin-4-ylamino)-3,3-dimethylbutyl ethanethioate, 76a, (1.00 g, 3.27 mmol) in methanol (20 mL) was added NaOMe (1.457 mL of 25% solution in MeOH, 6.540 mmol) and the solution was stirred at room temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue was dissolved in water (25 mL) and slowly acidified with 2N HCl to give a white precipitate that was extracted twice with EtOAc. The combined organic phases were dried (MgSO4), filtered and concentrated under reduced pressure to afford 0.85 g of the desired product as a pale beige color solid: LC/MS (10-90% ACN/water 5 min with 0.9% FA) m/z 264.92 (M+H) RT=3.32 min.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. dissolutionthe residue was dissolved in water (25 mL)
  3. customto give a white precipitate that
  4. extractionwas extracted twice with EtOAc
  5. dry with materialThe combined organic phases were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-1fe1bfa67a854ae293fc883765a7ae5e
Source dataset
uspto-grants-2016_07
Patent number
US09394302B2

Reaction notes

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