Sodium Thiosulfate → Ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-oxopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

HRID 1426987Notes

Reaction equation

HRID 1426987 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:50][CH3:51])=[C:28]([C@H:30]2[CH2:34][CH:33]([OH:35])[CH2:32][N:31]2[C:36]2[CH:41]=[CH:40][N:39]3[N:42]=[CH:43][C:44]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[C:38]3[N:37]=2)[CH:29]=1.[O-]S([O-])(=S)=O.[Na+].[Na+]>C(Cl)Cl>[F:23][C:24]1[CH:25]=[CH:26][C:27]([O:50][CH3:51])=[C:28]([CH:30]2[CH2:34][C:33](=[O:35])[CH2:32][N:31]2[C:36]2[CH:41]=[CH:40][N:39]3[N:42]=[CH:43][C:44]([C:45]([O:47][CH2:48][CH3:49])=[O:46])=[C:38]3[N:37]=2)[CH:29]=1

Participants

5

Reactant 3

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 86691712(R)-ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate

Product 1

HCID 86691759Ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-oxopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylateYield 82.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a suspension of Dess-Martin periodinane (0.233 g, 0.549 mmol) in CH2Cl2 (2.2 mL) at 0° C. was added a solution of (R)-ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-hydroxypyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.200 g, 0.499 mmol) in CH2Cl2 (1.5 mL). The resulting mixture was warmed to ambient temperature and stirred for 18 hours. The reaction mixture was cooled to 0° C. and quenched with saturated aqueous NaHCO3 (5 mL) containing Na2S2O3 (0.608 g, 3.85 mmol). The resulting mixture was warmed to ambient temperature and stirred for 10 minutes. The organic layer was separated, washed with saturated aqueous NaHCO3 (10 mL) followed by brine (10 mL), dried over MgSO4, filtered, and concentrated under reduced pressure to afford ethyl 5-(2-(5-fluoro-2-methoxyphenyl)-4-oxopyrrolidin-1-yl)pyrazolo[1,5-a]pyrimidine-3-carboxylate (0.164 g, 82.4% yield). LC/MS (ES+APCI) m/z=399.1 (M+H).

Workup

  1. temperatureThe reaction mixture was cooled to 0° C.
  2. customquenched with saturated aqueous NaHCO3 (5 mL)
  3. temperatureThe resulting mixture was warmed to ambient temperature
  4. stirringstirred for 10 minutes
  5. customThe organic layer was separated
  6. washwashed with saturated aqueous NaHCO3 (10 mL)
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-96637b95acf244d184188ae2de2f3a9b
Source dataset
uspto-grants-2015_01
Patent number
US08933084B2

Reaction notes

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