Potassium Carbonate → HCID 37967249, compound

HRID 1485576Notes

Reaction equation

HRID 1485576 reaction equation
[NH:1]1[CH2:6][CH2:5][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:13])([CH3:12])[CH3:11])[CH2:3][CH2:2]1.Cl[C:16]1[N:21]=[CH:20][CH:19]=[CH:18][N:17]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1>[N:17]1[CH:18]=[CH:19][CH:20]=[N:21][C:16]=1[N:1]1[CH2:2][CH2:3][CH:4]([NH:7][C:8](=[O:14])[O:9][C:10]([CH3:11])([CH3:13])[CH3:12])[CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 744042-ChloropyrimidineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 37967249HCID 37967249, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of tert-butyl piperidin-4-ylcarbamate (2.00 g, 9.99 mmol), 2-chloropyrimidine (3.43 g, 30.0 mmol), and K2CO3 (6.90 g, 49.9 mmol) in 1,4-dioxane (57 mL) was refluxed for 2 days. After cooled to room temperature, the mixture was filtered and washed with EtOAc. The filtrate was concentrated in vacuo, and the residue was purified by column chromatography (Hexane:EtOAC=3:1) to give tert-butyl 1-(pyrimidine-2-yl)piperidin-4-ylcarbamate (2.78 g, quant.) as a white solid. 1H-NMR (CDCl3, Varian 400 MHz) δ 1.23-1.44 (2H, m), 1.45 (9H, s), 1.95-2.08 (2H, m), 2.99-3.10 (2H, m), 3.72 (1H, brs), 4.39-4.53 (1H, m), 4.59-4.69 (2H, m), 6.47 (1H, t, J=4.8 Hz), 8.29 (2H, d, J=4.8 Hz). m/z=278.87 [M+1]+.

Workup

  1. temperaturewas refluxed for 2 days
  2. filtrationthe mixture was filtered
  3. washwashed with EtOAc
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue was purified by column chromatography (Hexane:EtOAC=3:1)

Sources & evidence

ORD record
ord-5a43d7eeca6b49e08594412c073fcd1d
Source dataset
uspto-grants-2016_08
Patent number
US09422298B2

Reaction notes

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