Potassium hydroxy sulfite → HCID 58298341, compound

HRID 425246Notes

Reaction equation

HRID 425246 reaction equation
[OH:1]OS([O-])=O.[K+].[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[CH:16]=[C:17]([C:27]([NH2:29])=[O:28])[N:18]3[C:23]([S:24][CH3:25])=[CH:22][C:21]([CH3:26])=[N:20][C:19]=23)=[C:10]([CH3:30])[CH:9]=1>O.C(O)C>[Br:7][C:8]1[CH:13]=[C:12]([CH3:14])[C:11]([C:15]2[CH:16]=[C:17]([C:27]([NH2:29])=[O:28])[N:18]3[C:23]([S:24]([CH3:25])=[O:1])=[CH:22][C:21]([CH3:26])=[N:20][C:19]=23)=[C:10]([CH3:30])[CH:9]=1

Participants

5

Reactant 2

HCID 23707502Potassium hydroxy sulfiteHCID 58298339HCID 58298339, compound

Product 1

HCID 58298341HCID 58298341, compoundYield 2,180.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

To a solution of Oxone (9.12 g) in water (50 mL) was added a solution of 8-(4-bromo-2,6-dimethyl-phenyl)-2-methyl-4-methylsulfanyl-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid amide (3.00 g) in ethanol (50 mL) in an ice-cooling bath. The reaction mixture was stirred under ice-cooling for 30 minutes, poured into water and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous sodium hydrogencarbonate and brine, dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated under reduced pressure and the residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: ethyl acetate) to give 8-(4-bromo-2,6-dimethyl-phenyl)-4-methanesulfinyl-2-methyl-pyrrolo[1,2-a]pyrimidine-6-carboxylic acid amide (1:68 g).

Workup

  1. temperaturecooling bath
  2. temperaturecooling for 30 minutes
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with a saturated aqueous sodium hydrogencarbonate and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe residue was purified by a silica gel column chromatography (silica gel: Wako Gel (C200), eluent: ethyl acetate)

Sources & evidence

ORD record
ord-fe1c4efe6cbe4cd59425184c915dfcc3
Source dataset
uspto-grants-2012_01
Patent number
US08106194B2

Reaction notes

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