Ammonium formate → HCID 178454030, compound

HRID 33362Notes

Reaction equation

HRID 33362 reaction equation
[C:1]([O:5][C:6](=[O:43])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]2[N:23]=[C:22]3[C:18]([N:19]=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH:26]=[CH:25]3)=[C:17]([NH:29][CH:30]3[CH2:35][CH2:34][N:33](CC4C=CC=CC=4)[CH2:32][CH2:31]3)[N:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2].C([O-])=O.[NH4+]>CO.O.[Pd]>[C:1]([O:5][C:6](=[O:43])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([NH:14][C:15]2[N:23]=[C:22]3[C:18]([N:19]=[CH:20][N:21]3[CH:24]3[CH2:28][CH2:27][CH:26]=[CH:25]3)=[C:17]([NH:29][CH:30]3[CH2:31][CH2:32][NH:33][CH2:34][CH2:35]3)[N:16]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 2723923Ammonium formateHCID 178454032HCID 178454032, compound

Product 1

HCID 178454030HCID 178454030, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Add to a solution of trans-{4-[6-(1-benzyl-piperidin-4-ylamino)-9-cyclopent-2-enyl-9H-purin-2-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (8c,1.0-mmol) in 40 mL of methanol, a suspension of Pd black (0.5 wt %) in a small amount of water. Then add a solution of ammonium formate (2.2 mmol) in 10 mL of water, and heat at a gentle reflux overnight. Remove the catalyst by filtration through Celite® and concentrate the filtrate. Dissolve the residue in DCM and extract with water. Remove the white precipitate by filtration through a pad of Celite®, wash the filtrate with brine, dry over sodium sulfate and filter. Concentrate the filtrate and purify the residue on silica gel (50 g) using DCM:methanol (4:1) to give trans-{4-[9-cyclopent-2-enyl-6-(piperidin-4-ylamino)-9H-purin-2-ylamino]-cyclohexyl}-carbamic acid tert-butyl ester (9c.

Workup

  1. temperatureheat at
  2. temperaturea gentle reflux overnight
  3. customRemove the catalyst
  4. filtrationby filtration through Celite®
  5. concentrationconcentrate the filtrate
  6. dissolutionDissolve the residue in DCM
  7. extractionextract with water
  8. customRemove the white precipitate
  9. filtrationby filtration through a pad of Celite®
  10. washwash the filtrate with brine
  11. dry with materialdry over sodium sulfate
  12. filtrationfilter
  13. concentrationConcentrate the filtrate
  14. custompurify the residue on silica gel (50 g)

Sources & evidence

ORD record
ord-ee46fa46da0b4a25bde068ad4a0bb74b
Source dataset
uspto-grants-2008_09
Patent number
US07429595B2

Reaction notes

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