(3-(benzyloxy)-5-fluorophenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine → 3-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-5-fluorophenol

HRID 731806Notes

Reaction equation

HRID 731806 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]([C:16]2[C:24]3[C:19](=[N:20][CH:21]=[N:22][C:23]=3[NH2:25])[N:18]([CH:26]([CH3:28])[CH3:27])[N:17]=2)[CH:12]=[C:13]([F:15])[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[NH2:25][C:23]1[N:22]=[CH:21][N:20]=[C:19]2[N:18]([CH:26]([CH3:28])[CH3:27])[N:17]=[C:16]([C:11]3[CH:10]=[C:9]([OH:8])[CH:14]=[C:13]([F:15])[CH:12]=3)[C:24]=12

Participants

4

Reactant 1

HCID 67406694(3-(benzyloxy)-5-fluorophenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine

Product 1

HCID 249053423-(4-amino-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-3-yl)-5-fluorophenolYield 130.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of -(3-(benzyloxy)-5-fluorophenyl)-1-isopropyl-1H-pyrazolo[3,4-d]pyrimidin-4-amine (15 mg, 0.04 mmol) in MeOH (0.9 ml) was flushed with argon. Pd on activated carbon (10 ml) was carefully added while keeping reaction under an argon atmosphere. Reaction was flushed with H2 gas and left under H2 atmosphere overnight at room temperature. The reaction was filtered through celite and rinsed with MeOH to yield BA22 (15 mg, 100% yield). ESI-MS (M+H)+ m/z calcd 288.1, found 288.1.

Workup

  1. customreaction under an argon atmosphere
  2. customReaction
  3. customwas flushed with H2 gas
  4. filtrationThe reaction was filtered through celite
  5. washrinsed with MeOH

Sources & evidence

ORD record
ord-42f46a297c554ef4a8d1278977c5aea2
Source dataset
uspto-grants-2009_09
Patent number
US07585868B2

Reaction notes

Loading…