Sodium Bicarbonate → HCID 12087786, compound

HRID 397366Notes

Reaction equation

HRID 397366 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[N:22]=3)=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=3)[N:13]=2)=[CH:5][CH:4]=1.[OH:29]OS([O-])=O.[K+].C([O-])(O)=O.[Na+]>C1COCC1.O>[CH3:1][S:2]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[NH:10][C:11]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([O:27][CH3:28])[N:22]=3)=[C:12]([C:14]3[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=3)[N:13]=2)=[CH:5][CH:4]=1)=[O:29]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 9952439HCID 9952439, compoundHCID 23707502Potassium hydroxy sulfite

Product 1

HCID 12087786HCID 12087786, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-(4-methylthiophenyl)-4-(4-fluorophenyl)-5-(2-methoxy-4-pyrimidinyl)imidazole (0.10 g, 0.25 mmol) in 10 mL of THF at 0° C. was added a cooled solution of Oxone (0.084 g, 0.28 mmol)in 10 mL of H2O. The solution was warmed to room temperature and stirred for 20 min. Next, 20 mL of NaHCO3 sat was added and the mixture was extracted thrice with 20 mL of CH2Cl2. The combined organic layers were washed with 20 mL of 20% NaS2O5 and brine and then dried over MgSO4, filtered and concentrated under reduced pressure. The resulting residue was then purified by silica gel chromatography with 2-6% CH3OH/CH2Cl2 to give the title compound as a light yellow solid (0.084 g, 82%). ES(+) MS m/e=409 (MH+)

Workup

  1. extractionthe mixture was extracted thrice with 20 mL of CH2Cl2
  2. washThe combined organic layers were washed with 20 mL of 20% NaS2O5 and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting residue was then purified by silica gel chromatography with 2-6% CH3OH/CH2Cl2

Sources & evidence

ORD record
ord-d0c46cecb6a24c268602c6afa43890b4
Source dataset
uspto-grants-2003_08
Patent number
US06610695B1

Reaction notes

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