Potassium Carbonate → 3-(5-Bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl ester

HRID 1094254Notes

Reaction equation

HRID 1094254 reaction equation
[NH2:1][CH:2]1[CH2:7][CH2:6][CH2:5][N:4]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:3]1.[Br:15][C:16]1[CH:17]=[N:18][C:19](Cl)=[N:20][CH:21]=1.C([O-])([O-])=O.[K+].[K+].CCN(C(C)C)C(C)C>CC1C=CC=CC=1C.CC(=O)OCC.CCCCCCC>[C:11]([O:10][C:8]([N:4]1[CH2:5][CH2:6][CH2:7][CH:2]([NH:1][C:19]2[N:20]=[CH:21][C:16]([Br:15])=[CH:17][N:18]=2)[CH2:3]1)=[O:9])([CH3:14])([CH3:13])[CH3:12]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 5458091-BOC-3-AminopiperidineHCID 6066655-Bromo-2-chloropyrimidine

Product 1

HCID 581854853-(5-Bromo-pyrimidin-2-ylamino)-piperidine-1-carboxylic acid tert-butyl esterYield 47.7%

Reagents, catalysts & solvents 2

HCID 7237O-XyleneSolventHCID 21899848Ethylacetate heptaneSolvent

Procedure

To a solution of (+/−)-3-amino-1-N-Boc-piperidine (1 g) in dry o-xylene (20 mL) were added successively 5-bromo-2-chloropyrimidine (965 mg), anhydrous K2CO3 (1.38 g), DIEA (3.42 mL). The reaction mixture was stirred at reflux for 3 d under nitrogen. After cooling to RT, the brown suspension was filtered and the filtrate was concentrated to yield a crude brown-orange oil. FC (EA/n-heptane: 3/7) gave 850 mg (46%) of the title compound as a light brown solid.

Workup

  1. temperatureat reflux for 3 d under nitrogen
  2. filtrationthe brown suspension was filtered
  3. concentrationthe filtrate was concentrated
  4. customto yield a crude brown-orange oil

Sources & evidence

ORD record
ord-89da8264e5b544099629a9846c193751
Source dataset
uspto-grants-2012_03
Patent number
US08133901B2

Reaction notes

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