Methanol → 2-(4-Fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-8-methylimidazo[1,2-a]pyrazine

HRID 2233087Notes

Reaction equation

HRID 2233087 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[N:14][CH:13]=[CH:12][N:11]3[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20](SC)[N:19]=2)=[CH:4][CH:3]=1.O[O:27][S:28]([O-:30])=O.[K+].[CH3:32]O>C(Cl)Cl.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([CH3:16])=[N:14][CH:13]=[CH:12][N:11]3[C:17]=2[C:18]2[CH:23]=[CH:22][N:21]=[C:20]([S:28]([CH3:32])(=[O:30])=[O:27])[N:19]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 887MethanolHCID 23707502Potassium hydroxy sulfiteHCID 574387482-(4-Fluorophenyl)-8-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Product 1

HCID 588695482-(4-Fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)-8-methylimidazo[1,2-a]pyrazineYield 38%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-(4-fluorophenyl)-8-methyl-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine (Example #F.1A; 8.58 g, 24.4 mmol) in MeOH (200 mL) and DCM (200 mL) at ambient temperature was added Oxone® (30.0 g, 48.8 mmol) in water (100 mL) to form a suspension. After about 20 h of stirring the layers were separated. The aqueous layer was washed with DCM (3×30 mL). Combined organic layers were washed with brine, dried over MgSO4, and concentrated under reduced pressure to yield a yellow solid, which was purified via FCC using EtOAc as an eluent. The product-containing fractions were combined and concentrated under reduced pressure to give a white solid (6.5 g) that was recrystallized in IPA (700 mL) to yield the title compound (3.6 g) after filtration. Additional product was observed in the filtrate. (3.6 g, 38% yield): LC/MS (Table 1, Method b) Rt=1.7 min; MS m/z: 384.1 (M+H)+.

Workup

  1. customat ambient temperature
  2. customto form a suspension
  3. customwere separated
  4. washThe aqueous layer was washed with DCM (3×30 mL)
  5. washCombined organic layers were washed with brine
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated under reduced pressure
  8. customto yield a yellow solid, which
  9. customwas purified via FCC
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a6e2710e4b114fb2b5bc36703dfa0892
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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