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

HRID 2233104Notes

Reaction equation

HRID 2233104 reaction equation
[CH:1]1([CH2:4][C:5]2[C:6]3[N:7]([C:11]([C:21]4[CH:26]=[CH:25][N:24]=[C:23](SC)[N:22]=4)=[C:12]([C:14]4[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=4)[N:13]=3)[CH:8]=[CH:9][N:10]=2)[CH2:3][CH2:2]1.O[O:30][S:31]([O-:33])=O.[K+].[C:35]([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl.CO.O>[CH:1]1([CH2:4][C:5]2[C:6]3[N:7]([C:11]([C:21]4[CH:26]=[CH:25][N:24]=[C:23]([S:31]([CH3:35])(=[O:33])=[O:30])[N:22]=4)=[C:12]([C:14]4[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=4)[N:13]=3)[CH:8]=[CH:9][N:10]=2)[CH2:2][CH2:3]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 23707502Potassium hydroxy sulfiteHCID 588695358-Cyclopropylmethyl-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrazine

Product 1

HCID 588695518-Cyclopropylmethyl-2-(4-fluorophenyl)-3-(2-methanesulfonylpyrimidin-4-yl)imidazo[1,2-a]pyrazineYield 85%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 8-cyclopropylmethyl-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrazine (5.16 g, 13.2 mmol) in DCM (50 mL) and MeOH (50 mL) was added a solution of Oxone® (16.2 g, 26.4 mmol) in water (50 mL). After about 4 h of rapid stirring, the mixture was neutralized with saturated Na2CO3 solution and extracted with DCM. The combined organic phase was dried over Na2SO4 and concentrated. The crude material was purified by silica gel chromatography with heptane/EtOAc (gradient 50-100% EtOAc). After concentration, the residue was three times re-dissolved in DCM and re-concentrated to give 4.77 g (85%) of the title compound as a yellowish solid: LC/MS (Table 1, Method g) Rt=2.68 min; MS m/z: 424.1 (M+H)+.

Workup

  1. extractionextracted with DCM
  2. dry with materialThe combined organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe crude material was purified by silica gel chromatography with heptane/EtOAc (gradient 50-100% EtOAc)
  5. concentrationAfter concentration
  6. dissolutionre-dissolved in DCM
  7. concentrationre-concentrated

Sources & evidence

ORD record
ord-4872f388b23949c1b64f44e98b9f77e5
Source dataset
uspto-grants-2010_05
Patent number
US07709468B2

Reaction notes

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