Hydrochloric Acid → HCID 178521095, compound

HRID 230190Notes

Reaction equation

HRID 230190 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[F:34])=[N:14][C:15]=2[O:17][CH2:18][C@H:19]2[CH2:23][O:22]C(C)(C)[O:20]2)[NH:10][N:9]=1.Cl>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:16]2[C:11](=[N:12][C:13]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][C:28]=3[F:34])=[N:14][C:15]=2[O:17][CH2:18][C@@H:19]([OH:20])[CH2:23][OH:22])[NH:10][N:9]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 178431482(S)-3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 178521095HCID 178521095, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

(S)-3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-4-(2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-1H-pyrazolo[3,4-d]pyrimidine (1.395 g) was taken up in 30 mL dioxane, and 25 mL of 4N HCl was added. The reaction mixture was stirred at room temperature for 25 minutes, and then the reaction mixture was partitioned between water (100 mL) and EtOAc (300 mL). The organic phase was washed with brine, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was eluted through silica gel with 30% EtOAc in methylene chloride to provide 886.4 mg of (S)-3-[3-(2-Chloro-phenyl)-6-(2,4-difluoro-phenoxy)-1H-pyrazolo[3,4-d]pyrimidin-4-yloxy]-propane-1,2-diol. Mass Spec. M+H=449. Mp.=179.2-181.3° C.

Workup

  1. customthe reaction mixture was partitioned between water (100 mL) and EtOAc (300 mL)
  2. washThe organic phase was washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. washThe residue was eluted through silica gel with 30% EtOAc in methylene chloride

Sources & evidence

ORD record
ord-8984ae06f917426cb930ef66ad6856a7
Source dataset
uspto-grants-2009_07
Patent number
US07566708B2

Reaction notes

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