HCID 86667974, compound → HCID 68107213, compound

HRID 2403606Notes

Reaction equation

HRID 2403606 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)[C:3]=1[CH3:21]>CCO.[Pd]>[CH3:21][C:3]1[C:4]([N:8]2[CH2:13][CH2:12][N:11]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH2:10][CH2:9]2)=[N:5][CH:6]=[N:7][CH:2]=1

Participants

4

Reactant 1

HCID 86667974HCID 86667974, compound

Product 1

HCID 68107213HCID 68107213, compoundYield 71.6%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

tert-Butyl 4-(6-chloro-5-methylpyrimidin-4-yl)piperazine-1-carboxylate (400 mg) was dissolved in EtOH (8 ml), and 10% Pd/C (40 mg) was added thereto, followed by stirring at room temperature overnight under a hydrogen atmosphere. To the reaction mixture was added TEA (129 mg) and filtered using Celite as a filtration assistant, and the filtrate was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (10% to 80% EtOAc/hexane) to obtain tert-butyl 4-(5-methylpyrimidin-4-yl)piperazine-1-carboxylate (255 mg).

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated under reduced pressure
  3. customThe obtained residue was purified by silica gel column chromatography (10% to 80% EtOAc/hexane)

Sources & evidence

ORD record
ord-aec1564deece466da34db040b2f01abe
Source dataset
uspto-grants-2014_08
Patent number
US08802679B2

Reaction notes

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