Acetone → 3-(4-Chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)propane-1,2-diol

HRID 244456Notes

Reaction equation

HRID 244456 reaction equation
C([N:4]1[C:12]2[C:11]([Cl:13])=[N:10][CH:9]=[N:8][C:7]=2[C:6]([C:14]([C:20]2[CH:21]=[C:22]3[C:26](=[CH:27][CH:28]=2)[N:25]([C:29]2[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=2)[N:24]=[CH:23]3)([OH:19])[C:15]([F:18])([F:17])[F:16])=[CH:5]1)C=C.[O-:36][Mn](=O)(=O)=O.[K+].[CH3:42][C:43]([CH3:45])=[O:44]>O>[Cl:13][C:11]1[C:12]2[N:4]([CH2:42][CH:43]([OH:44])[CH2:45][OH:36])[CH:5]=[C:6]([C:14]([C:20]3[CH:21]=[C:22]4[C:26](=[CH:27][CH:28]=3)[N:25]([C:29]3[CH:34]=[CH:33][C:32]([F:35])=[CH:31][CH:30]=3)[N:24]=[CH:23]4)([OH:19])[C:15]([F:18])([F:16])[F:17])[C:7]=2[N:8]=[CH:9][N:10]=1

Participants

5

Reactant 3

HCID 180Acetone2×HCID 516875Potassium PermanganateHCID 594371991-(5-Allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol

Product 1

HCID 249579933-(4-Chloro-7-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}pyrrolo[3,2-d]pyrimidin-5-yl)propane-1,2-diolYield 44%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a room temperature solution of 1-(5-allyl-4-chloro-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethanol (245 mg, 0.5 mmol, 1 equiv.) in 4 mL of acetone and 2 mL of water was added a solution of KMnO4 in 1 mL of water and 2 mL of acetone. After 3 hours, the mixture was filtered and the filter cake washed with acetone. The filtrate was concentrated and the residue diluted with water and extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo. The residue was purified by HPLC (5-85% CH3CN/water 0.1% TFA). The desired peaks were combined and made basic with saturated aqueous sodium bicarbonate. The CH3CN was removed and the aqueous was extracted with EtOAc. The combined organic layers were dried, filtered, and concentrated in vacuo to provide 116 mg (44%) of the title compound as a white solid. MS m/z 536.10 (MH+).

Workup

  1. filtrationthe mixture was filtered
  2. washthe filter cake washed with acetone
  3. concentrationThe filtrate was concentrated
  4. additionthe residue diluted with water
  5. extractionextracted with EtOAc
  6. customThe combined organic layers were dried
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was purified by HPLC (5-85% CH3CN/water 0.1% TFA)
  10. customThe CH3CN was removed
  11. extractionthe aqueous was extracted with EtOAc
  12. customThe combined organic layers were dried
  13. filtrationfiltered
  14. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5085fd1e793544ed9981f07d2d688eb8
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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