Sodium Bicarbonate → 4-(2-(Methylsulfinyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide

HRID 1052046Notes

Reaction equation

HRID 1052046 reaction equation
[F:1][C:2]([F:30])([F:29])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[CH:17]=[C:16]([N:18]3[CH2:26][C:25]4[CH:24]=[N:23][C:22]([S:27][CH3:28])=[N:21][C:20]=4[CH2:19]3)[CH:15]=[CH:14][N:13]=2)=[O:11])[CH:6]=[CH:7][CH:8]=1.S([O-])(O[O-])(=O)=[O:32].[K+].[K+].[S:39](=[O:42])(O)[O-:40].[Na+].[C:44](=O)(O)[O-].[Na+]>O1CCCC1.O>[CH3:28][S:27]([C:22]1[N:23]=[CH:24][C:25]2[CH2:26][N:18]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:29])[F:30])[CH:4]=4)=[O:11])[CH:17]=3)[CH2:19][C:20]=2[N:21]=1)=[O:32].[CH3:44][S:39]([C:22]1[N:23]=[CH:24][C:25]2[CH2:26][N:18]([C:16]3[CH:15]=[CH:14][N:13]=[C:12]([C:10]([NH:9][C:5]4[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:29])([F:1])[F:30])[CH:4]=4)=[O:11])[CH:17]=3)[CH2:19][C:20]=2[N:21]=1)(=[O:42])=[O:40]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 10313463Potassium peroxymonosulphateHCID 23665763Sodium BisulfiteHCID 866958544-(2-Methylsulfanyl-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid (3-trifluoromethyl-phenyl)-amide

Product 2

HCID 866958324-(2-(Methylsulfinyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamideHCID 866958334-(2-(methylsulfonyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A slurry of 4-(2-Methylsulfanyl-5,7-dihydro-pyrrolo[3,4-d]pyrimidin-6-yl)-pyridine-2-carboxylic acid (3-trifluoromethyl-phenyl)-amide (120 mg, 0.28 mmol) and potassium peroxomonosulfate (Oxone®, 184 mg, 0.30 mmol) in tetrahydrofuran (10 mL) and water (4 mL) was stirred at room temperature for 16 hours. To the reaction was added saturated aqueous sodium bisulfite and saturated aqueous sodium bicarbonate to adjust the pH to 7. The mixture was extracted with chloroform. The extract was washed with water, dried (MgSO4), filtered and evaporated. The resulting solid was dissolved in dichloromethane:methanol (19:1), filtered and applied to chromatography on silica gel (12 g) and eluted with dichloromethane:methanol (19:1) and gave the title compound (15 mg, 0.032 mmol) and 4-(2-(methylsulfonyl)-5H-pyrrolo[3,4-d]pyrimidin-6(7H)-yl)-N-(3-(trifluoromethyl)phenyl)picolinamide (18 mg, 0.040 mmol).

Workup

  1. extractionThe mixture was extracted with chloroform
  2. washThe extract was washed with water
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe resulting solid was dissolved in dichloromethane:methanol (19:1)
  7. filtrationfiltered
  8. washeluted with dichloromethane:methanol (19:1)

Sources & evidence

ORD record
ord-303be36af7ed4d5fa4129a7e1adbc587
Source dataset
uspto-grants-2016_07
Patent number
US09388176B2

Reaction notes

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