Sodium Carbonate → 2-(4-Fluorophenyl)-8-isopropoxy-3-(2-methanesulfonylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

HRID 2233114Notes

Reaction equation

HRID 2233114 reaction equation
O[O:2][S:3]([O-:5])=O.[K+].[F:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]3[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[N:20][CH:19]=[CH:18][N:17]3[C:26]=2[C:27]2[CH:32]=[CH:31][N:30]=[C:29](SC)[N:28]=2)=[CH:10][CH:9]=1.[C:35]([O-])([O-])=O.[Na+].[Na+]>O.C(Cl)Cl.CO>[F:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15]=[C:16]3[C:21]([O:22][CH:23]([CH3:25])[CH3:24])=[N:20][CH:19]=[CH:18][N:17]3[C:26]=2[C:27]2[CH:32]=[CH:31][N:30]=[C:29]([S:3]([CH3:35])(=[O:5])=[O:2])[N:28]=2)=[CH:12][CH:13]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 574387762-(4-Fluorophenyl)-8-isopropoxy-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine

Product 1

HCID 588695382-(4-Fluorophenyl)-8-isopropoxy-3-(2-methanesulfonylpyrimidin-4-yl)-imidazo[1,2-a]pyrazineYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

A solution of Oxone® (3.17 g, 5.15 mmol) in water (9 mL) was added to a solution of 2-(4-fluoro-phenyl)-8-isopropoxy-3-(2-methylsulfanylpyrimidin-4-yl)-imidazo[1,2-a]pyrazine (1.02 g, 2.57 mmol) in 41 mL of DCM/MeOH (1:1). The resulting reaction mixture was stirred overnight at ambient temperature, neutralized with a saturated aqueous solution of Na2CO3, and extracted with DCM. The organic phase was dried over MgSO4, filtered, and concentrated. The crude material was sequentially triturated with MeOH and ACN to give 0.387 g (35%) of the title compound: LC/MS (Table 1, Method g) Rt=2.69 min; MS m/z: 428.2 (M+H)+.

Workup

  1. customThe resulting reaction mixture
  2. extractionextracted with DCM
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude material was sequentially triturated with MeOH and ACN

Sources & evidence

ORD record
ord-2971353b73d9472d9124cf70f732e412
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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