HCID 23503394, compound → HCID 23503382, compound

HRID 1292864Notes

Reaction equation

HRID 1292864 reaction equation
[CH2:1]([NH:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[C:14]([N:20]3[CH:24]=[CH:23][C:22]([C:25]4[CH:30]=[CH:29][C:28]([CH:31]=[CH2:32])=[CH:27][CH:26]=4)=[N:21]3)[N:15]2[CH2:18][CH3:19])=[C:11]([NH2:33])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>CO.[Pd]>[CH2:1]([NH:8][C:9]1[N:17]=[C:16]2[C:12]([N:13]=[C:14]([N:20]3[CH:24]=[CH:23][C:22]([C:25]4[CH:26]=[CH:27][C:28]([CH2:31][CH3:32])=[CH:29][CH:30]=4)=[N:21]3)[N:15]2[CH2:18][CH3:19])=[C:11]([NH2:33])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 23503394HCID 23503394, compound

Product 1

HCID 23503382HCID 23503382, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

N2 benzyl-8-[3-(4-vinylphenyl)pyrazol-1-yl]-9-ethyl-9H-purine-2,6-diamine, a compound of Formula I (25 mg, 0.05 mmoles), was dissolved in methanol (2 mL), and to this solution was added 20% w/w Pd/C. The reaction mixture was stirred at room temperature under hydrogen at 1 atmosphere. After 2 hours, the reaction mixture was filtered over celite, solvent evaporated under reduced pressure, and the residue obtained was purified by preparative TLC (eluting with 1:1 EtOAc:Hexanes) to give N2 benzyl-8-[3-(4-ethylphenyl)pyrazol-1-yl]-9-ethyl-9H-purine-2,6-diamine as a yellow solid. Similarly, reduction of N2 benzyl-8-[4-allylpyrazol-1-yl]-9-ethyl-9H-purine-2,6-diamine affords N2 benzyl-8-[4-propylpyrazol-1-yl]-9-ethyl-9H-purine-2,6-diamine.

Workup

  1. filtrationthe reaction mixture was filtered over celite, solvent
  2. customevaporated under reduced pressure
  3. customthe residue obtained
  4. customwas purified by preparative TLC (eluting with 1:1 EtOAc:Hexanes)

Sources & evidence

ORD record
ord-6a36e00b3b884d3dafcfc05acd46b31f
Source dataset
uspto-grants-2007_07
Patent number
US07238700B2

Reaction notes

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