6-Chloropurine → HCID 178525138, compound

HRID 1827117Notes

Reaction equation

HRID 1827117 reaction equation
[NH2:1][CH2:2][CH:3]1[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:10])[CH2:5][CH2:4]1.Cl[C:20]1[N:28]=[CH:27][N:26]=[C:25]2[C:21]=1[NH:22][CH:23]=[N:24]2>CN(C=O)C.C([O-])(O)=O.[Na+]>[N:28]1[C:20]([NH:1][CH2:2][CH:3]2[CH2:8][CH2:7][N:6]([C:9]([O:11][CH2:12][C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:10])[CH2:5][CH2:4]2)=[C:21]2[C:25]([NH:24][CH:23]=[N:22]2)=[N:26][CH:27]=1

Participants

5

Reactant 2

HCID 53592776-ChloropurineHCID 219554994-Aminomethyl-1-N-Cbz-piperidine

Product 1

HCID 178525138HCID 178525138, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 516892Sodium BicarbonateSolvent

Procedure

In DMF (5 mL), benzyl 4-(aminomethyl)-1-piperidinecarboxylate (1.20 g, 4.83 mmol) and 6-chloropurine (448 mg, 2.49 mmol) were combined and treated with TEA in a single portion and aged under N2 at 100° C. for 18 h. The resulting reaction was diluted with sat. NaHCO3 and extracted with ethyl acetate (3×). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo to give a brown oil which was purified by silica gel chromatography (20 g, 32–60 μm silica, 99:1:0.1 to 90:10:1 CH2Cl2:CH3OH:NH4OH) to give benzyl 4-[(9H-purin-6-ylamino)methyl]-1-piperidinecarboxylate as a brown oil.

Workup

  1. additiontreated with TEA in a single portion
  2. customThe resulting reaction
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organics were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a brown oil which
  9. customwas purified by silica gel chromatography (20 g, 32–60 μm silica, 99:1:0.1 to 90:10:1 CH2Cl2:CH3OH:NH4OH)

Sources & evidence

ORD record
ord-5fc47ceb49de47baa5ebe9e5beae7a9d
Source dataset
uspto-grants-2006_05
Patent number
US07053089B2

Reaction notes

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