Tetrahydrofuran → 2-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]ethanol

HRID 1952357Notes

Reaction equation

HRID 1952357 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH2:16][C:17](OC)=[O:18])=[N:8]1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1COCC1.[OH-].[Na+]>O>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:11]2=[N:12][CH:13]=[CH:14][CH:15]=[C:10]2[C:9]([CH2:16][CH2:17][OH:18])=[N:8]1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 59529754Methyl [1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate

Product 1

HCID 685070442-[1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]ethanol

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

To a solution methyl [1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-3-yl]acetate (128 mg, 0.465 mmol) at 0° C. was added 2M LAH in THF (232 ul, 0.465 mmol) and stirred at 0° C. for 30 minutes. After this time, the reaction mixture was sequentially treated with water (18 ul) and 1.0N NaOH (54 ul) and stirred at 25° C. for 30 minutes. After this time, the mixture was filtered through celite and rinsing with THF. The filtrates were combined and the solvent evaporated in vacuo. The residue was purified by chromatography using RediSep column (12 g) and eluting with a gradient of 0-10% MeOH/CH2Cl2 to give the title compound. LRMS (M+1): 164.0.

Workup

  1. stirringstirred at 25° C. for 30 minutes
  2. filtrationAfter this time, the mixture was filtered through celite
  3. washrinsing with THF
  4. customthe solvent evaporated in vacuo
  5. customThe residue was purified by chromatography
  6. washeluting with a gradient of 0-10% MeOH/CH2Cl2

Sources & evidence

ORD record
ord-c980395374c74ce087ba47e3e3975c5b
Source dataset
uspto-grants-2013_03
Patent number
US08404856B2

Reaction notes

Loading…