Ammonium formate → HCID 86684820, compound

HRID 2202783Notes

Reaction equation

HRID 2202783 reaction equation
C([N:8]1[CH:13]2[CH2:14][CH2:15][CH:9]1[CH2:10][C:11]([C:17]1[C:22]([Br:23])=[CH:21][N:20]=[CH:19][N:18]=1)([OH:16])[CH2:12]2)C1C=CC=CC=1.C([O-])=O.[NH4+]>O.[Pd]>[Br:23][C:22]1[C:17]([C:11]2([OH:16])[CH2:12][CH:13]3[NH:8][CH:9]([CH2:15][CH2:14]3)[CH2:10]2)=[N:18][CH:19]=[N:20][CH:21]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67462540HCID 67462540, compound

Product 1

HCID 86684820HCID 86684820, compoundYield 44%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

8-Benzyl-3-(5-bromo-pyrimidin-4-yl)-8-aza-bicyclo[3.2.1]octan-3-ol (0.90 g, 2.4 mmol) was dissolved in IMS (20 mL) and water (1 mL). Palladium on carbon (10%; 0.40 g) was added under nitrogen. Ammonium formate (1.5 g, 24 mmol) was added and the mixture heated at reflux for 0.5 hour. The mixture was allowed to cool, filtered and the solvent removed by evaporation under vacuum. The residues were passed through an SCX cartridge, eluting with 2 M ammonia in methanol to give the title compound as a colourless oil (0.30 g).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 0.5 hour
  3. temperatureto cool
  4. filtrationfiltered
  5. customthe solvent removed by evaporation under vacuum
  6. washeluting with 2 M ammonia in methanol

Sources & evidence

ORD record
ord-bc62b9df888a42cba3c0b83b9e1cc010
Source dataset
uspto-grants-2016_06
Patent number
US09365564B2

Reaction notes

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