Sodium Thiosulfate → 1-[4-[3-Oxo-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide

HRID 928621Notes

Reaction equation

HRID 928621 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[OH:23][CH:24]1[CH2:30][CH:29]2[N:31]([C:32]3[C:33]4[C:48]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)=[CH:47][S:46][C:34]=4[N:35]=[C:36]([N:38]4[CH2:42][CH2:41][CH:40]([C:43]([NH2:45])=[O:44])[CH2:39]4)[N:37]=3)[CH:26]([CH2:27][CH2:28]2)[CH2:25]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl>[O:23]=[C:24]1[CH2:30][CH:29]2[N:31]([C:32]3[C:33]4[C:48]([C:49]5[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=5)=[CH:47][S:46][C:34]=4[N:35]=[C:36]([N:38]4[CH2:42][CH2:41][CH:40]([C:43]([NH2:45])=[O:44])[CH2:39]4)[N:37]=3)[CH:26]([CH2:27][CH2:28]2)[CH2:25]1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 895795001-[4-[3-Hydroxy-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide

Product 1

HCID 895796391-[4-[3-Oxo-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamideYield 115.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Dess-Martin Periodinane (50 mg, 0.12 mmol) was added to a suspension of 1-[4-[3-hydroxy-8-azabicyclo[3.2.1]octan-8-yl]-5-phenyl-thieno[2,3-d]pyrimidin-2-yl]pyrrolidine-3-carboxamide (40 mg, 0.089 mmol) in dichloromethane (4 mL). The mixture was stirred overnight at room temperature. Saturated aqueous sodium thiosulfate solution (2 mL) was added and the layers were separated. The aqueous was extracted with dichloromethane (2×2 mL). The combined organic layers were washed with saturated aqueous sodium bicarbonate solution (1×2 mL), filtered through a hydrophobic frit and evaporated to give the target compound as a white solid (46 mg). m/z [M+H]+448.1. Retention time 3.59 min (LCMS method+ve 6 min).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous was extracted with dichloromethane (2×2 mL)
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate solution (1×2 mL)
  4. filtrationfiltered through a hydrophobic frit
  5. customevaporated

Sources & evidence

ORD record
ord-259c981b70a54db8b185bab608f16775
Source dataset
uspto-grants-2016_03
Patent number
US09290511B2

Reaction notes

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