Potassium Carbonate → HCID 86593680, compound

HRID 18101Notes

Reaction equation

HRID 18101 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]1[CH2:14][NH2:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:18]=[N:19][C:20](Cl)=[N:21][CH:22]=1.C(=O)([O-])[O-:25].[K+].[K+].C(N(C(C)C)CC)(C)C>C1(C)C(C)=CC=CC=1>[C:6](=[O:7])([OH:25])[O:5][C:1]([CH3:4])([CH3:3])[CH3:2].[Br:16][C:17]1[CH:18]=[N:19][C:20]([NH:15][CH2:14][C@@H:9]2[CH2:10][CH2:11][CH2:12][CH2:13][N:8]2[C:6]([OH:5])=[O:7])=[N:21][CH:22]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 81531DiisopropylethylamineHCID 6066655-Bromo-2-chloropyrimidineHCID 1502020tert-Butyl (2S)-2-(aminomethyl)piperidine-1-carboxylate

Product 1

HCID 86593680HCID 86593680, compoundYield 141.5%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

(S)-2-Aminomethyl-piperidine-1-carboxylic acid tert butyl ester (1 g), 5-bromo-2-chloropyrimidine (0.9 g) were combined in xylene (20 ml) containing potassium carbonate (1.29 g) and diisopropylethylamine (2.43 g) and warmed to reflux for 48 h. The mixture was cooled to room temperature, filtered and solvent removed at reduced pressure. The residue was column chromatographed (silica gel, pentane-25% ethyl acetate/pentane). The appropriate fractions were collected, solvent removed at reduced pressure to give the title compound (1.43 g) as a colourless gum

Workup

  1. temperaturewarmed
  2. temperatureto reflux for 48 h
  3. filtrationfiltered
  4. customsolvent removed at reduced pressure
  5. customchromatographed (silica gel, pentane-25% ethyl acetate/pentane)
  6. customThe appropriate fractions were collected
  7. customsolvent removed at reduced pressure

Sources & evidence

ORD record
ord-a6228d3a902945a296a944fa031d5829
Source dataset
uspto-grants-2010_06
Patent number
US07741329B2

Reaction notes

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