Tetrahydrofuran → HCID 59311517, compound

HRID 1693282Notes

Reaction equation

HRID 1693282 reaction equation
C(C1[C:13]2[C:8](=[N:9][C:10]([N:15]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[N:11][C:12]=2[Cl:14])[N:7]([CH2:30][C:31]2[C:36]([CH3:37])=[C:35]([O:38][CH3:39])[C:34]([CH3:40])=[CH:33][N:32]=2)[N:6]=1)CC=C.C[N+]1([O-])CC[O:45][CH2:44]C1.[O:49]1[CH2:53][CH2:52][CH2:51][CH2:50]1.S([O-])([O-])(=O)=S.[Na+].[Na+]>[Os](=O)(=O)(=O)=O.C(OCC)(=O)C.O.CC(C)=O>[Cl:14][C:12]1[N:11]=[C:10]([N:15]([C:16]([O:18][C:19]([CH3:21])([CH3:22])[CH3:20])=[O:17])[C:23]([O:25][C:26]([CH3:27])([CH3:29])[CH3:28])=[O:24])[N:9]=[C:8]2[N:7]([CH2:30][C:31]3[C:36]([CH3:37])=[C:35]([O:38][CH3:39])[C:34]([CH3:40])=[CH:33][N:32]=3)[N:6]=[C:50]([CH2:51][CH2:52][CH:53]([OH:49])[CH2:44][OH:45])[C:13]=12

Participants

9

Reactant 4

HCID 8028TetrahydrofuranHCID 24477Sodium ThiosulfateHCID 82029Methyl morpholine oxideHCID 59311420HCID 59311420, compound

Product 1

HCID 59311517HCID 59311517, compoundYield 91%

Reagents, catalysts & solvents 4

HCID 30318Osmium TetroxideCatalystHCID 180AcetoneSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

Osmium tetroxide (21 mg) was added to a mixture composed of the above 3-(3-butenyl)-6-di(tert-butoxycarbonyl)amino-4-chloro-1-(4-methoxy-3,5-dimethylpyridin-2-yl)methyl-1H-pyrazolo[3,4-d]pyrimidine (4.78 g), N-methylmorpholine-N-oxide (5.04 g), tetrahydrofuran (60 mL), acetone (60 mL) and water (60 mL), and the mixture was stirred at room temperature for five hours. Ethyl acetate (300 mL) and a 10% sodium thiosulfate solution (500 mL) were added to the reaction mixture, followed by further stirring for 30 minutes. The reaction mixture was separated, and the aqueous layer was extracted with ethyl acetate. Then, the combined organic layers were washed with brine. The organic layers were dried over anhydrous sodium sulfate and then filtered. The filtrate was concentrated under reduced pressure and the solvent was evaporated to obtain a crude product of the title compound (4.60 g, 91%) as a solid. The resulting compound was directly used for the next reaction without purification.

Workup

  1. stirringby further stirring for 30 minutes
  2. customThe reaction mixture was separated
  3. extractionthe aqueous layer was extracted with ethyl acetate
  4. washThen, the combined organic layers were washed with brine
  5. dry with materialThe organic layers were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationThe filtrate was concentrated under reduced pressure
  8. customthe solvent was evaporated

Sources & evidence

ORD record
ord-d45f547a413b4699adc74207213f1fbe
Source dataset
uspto-grants-2012_04
Patent number
US08158638B2

Reaction notes

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