tert-Butyl (1-(2-chloropyrimidin-4-yl)piperidin-4-yl)carbamate → tert-Butyl (1-(pyrimidin-4-yl)piperidin-4-yl)carbamate

HRID 18510Notes

Reaction equation

HRID 18510 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[C:16](Cl)[N:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>C(O)C.C(O)(=O)C.[Pd]>[C:1]([O:5][C:6](=[O:21])[NH:7][CH:8]1[CH2:13][CH2:12][N:11]([C:14]2[CH:19]=[CH:18][N:17]=[CH:16][N:15]=2)[CH2:10][CH2:9]1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 50742435tert-Butyl (1-(2-chloropyrimidin-4-yl)piperidin-4-yl)carbamate

Product 1

HCID 53426887tert-Butyl (1-(pyrimidin-4-yl)piperidin-4-yl)carbamate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolventHCID 702EthanolSolvent

Procedure

To a solution of 395 mg [1-(2-Chloro-pyrimidin-4-yl)-piperidin-4-yl]-carbamic acid tert-butyl ester in 10 mL ethanol and 0.3 mL acetic acid, 20 mg Pd/C (10%) were added and the mixture purged with argon for 10 min. Then the mixture was stirred under a hydrogen atmosphere for 5 h at RT. After addition of 10 mL ethyl acetate the reaction mixture was filtered through a pad of celite. The solvent was evaporated under reduced pressure and the residue codistilled twice with toluene to give the product as a white solid. Yield: 468 mg.

Workup

  1. customthe mixture purged with argon for 10 min
  2. additionAfter addition of 10 mL ethyl acetate the reaction mixture
  3. filtrationwas filtered through a pad of celite
  4. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-6ba8c56a92e746c493d7340aee1b3076
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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