HCID 24959895, compound → HCID 178515632, compound

HRID 1946997Notes

Reaction equation

HRID 1946997 reaction equation
C([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH:24][CH:25]3[CH2:30][CH2:29][CH:28]([OH:31])[CH2:27][CH2:26]3)[N:19]=1)[CH:13]=[CH:12]2)C1C=CC=CC=1>CCO.[Pd]>[OH:31][C@H:28]1[CH2:29][CH2:30][C@H:25]([NH:24][C:20]2[N:19]=[C:18]([N:14]3[C:15]4[C:11](=[CH:10][C:9]([OH:8])=[CH:17][CH:16]=4)[CH:12]=[CH:13]3)[CH:23]=[CH:22][N:21]=2)[CH2:26][CH2:27]1

Participants

4

Reactant 1

HCID 24959895HCID 24959895, compound

Product 1

HCID 178515632HCID 178515632, compoundYield 93.1%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 4-[4-(5-benzyloxyindol-1-yl)-pyrimidin-2-ylamino]-cyclohexanol (70 mg) and Pd/C (15%, 38 mg) in EtOH was stirred under H2 (balloon pressure) at RT for 4 days. The reaction mixture was then filtered through a CELITE™ pad, the filter cake washed with EtOH, and the filtrate evaporated under reduced pressure. The residue was purified by flash chromatography (DCM/MeOH, 95:5) to give trans-1-[2-(4-hydroxy-cyclohexylamino)-pyrimidin-4-yl]-1H-indol-5-ol (51 mg) as an off-white solid. MS=325 [M+H]+; MP=246.5-248.0° C.

Workup

  1. filtrationThe reaction mixture was then filtered through a CELITE™ pad
  2. washthe filter cake washed with EtOH
  3. customthe filtrate evaporated under reduced pressure
  4. customThe residue was purified by flash chromatography (DCM/MeOH, 95:5)

Sources & evidence

ORD record
ord-3667e19b47614e93b9801d8fa67aff91
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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