6-(4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine → HCID 58483585, compound

HRID 68723Notes

Reaction equation

HRID 68723 reaction equation
C([N:14]1[CH2:17][CH:16]([N:18]2[CH2:23][CH2:22][N:21]([C:24]3[N:29]=[C:28]4[N:30]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:31]=[C:32]([CH2:33][CH3:34])[C:27]4=[CH:26][N:25]=3)[CH2:20][CH2:19]2)[CH2:15]1)(C1C=CC=CC=1)C1C=CC=CC=1>C(O)(=O)C.[OH-].[OH-].[Pd+2].Cl[Pd]Cl>[NH:14]1[CH2:15][CH:16]([N:18]2[CH2:19][CH2:20][N:21]([C:24]3[N:29]=[C:28]4[N:30]([C:35]5[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=5)[N:31]=[C:32]([CH2:33][CH3:34])[C:27]4=[CH:26][N:25]=3)[CH2:22][CH2:23]2)[CH2:17]1

Participants

5

Reactant 1

HCID 674479546-(4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

Product 1

HCID 58483585HCID 58483585, compound

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 9942167Palladium hydroxideCatalystHCID 176Acetic AcidSolvent

Procedure

A 100-mL round-bottom flask was purged, flushed and maintained with a hydrogen atmosphere, then, was added a solution of 6-(4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (400 mg, 0.76 mmol, 1.00 equiv) in acetic acid (20 mL) at room temperature. To the resulting mixture was then added Pd(OH)2 (50 mg, 0.4 mmol, 0.5 equiv), in portions at room temperature, followed by PdCl2 (50 mg, 0.28 mmol, 0.37 equiv), in portions at room temperature. The resulting solution was stirred overnight at room temperature. The solids were filtered out. The resulting mixture was concentrated under vacuum. The resulting residue (250 mg) was purified by Prep-HPLC with the following conditions (Gilson Pre-HPLC): Column, SHISEIDO, CAPCELL PAK C18, 20 mm ID*250 mm, 5 u; mobile phase, methanol/H2O; Detector, UV 254 nm, to yield 6-(4-(azetidin-3-yl)piperazin-1-yl)-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine as a white solid.

Workup

  1. customA 100-mL round-bottom flask was purged
  2. customflushed
  3. temperaturemaintained with a hydrogen atmosphere
  4. customat room temperature
  5. filtrationThe solids were filtered out
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. customThe resulting residue (250 mg) was purified by Prep-HPLC with the following conditions (Gilson Pre-HPLC)

Sources & evidence

ORD record
ord-290367fa991c4689a09b4f39cececd9d
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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