Benzyl 4-(pyrimidin-4-yl-methyl)piperazine-1-carboxylate → 4-(Piperazin-1-ylmethyl)pyrimidine

HRID 1804625Notes

Reaction equation

HRID 1804625 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][N:8]2[CH2:13][CH2:12][N:11](C(OCC3C=CC=CC=3)=O)[CH2:10][CH2:9]2)=[N:3][CH:2]=1.[H][H]>[Pd].CO>[N:8]1([CH2:7][C:4]2[CH:5]=[CH:6][N:1]=[CH:2][N:3]=2)[CH2:9][CH2:10][NH:11][CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 67518105Benzyl 4-(pyrimidin-4-yl-methyl)piperazine-1-carboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 639850394-(Piperazin-1-ylmethyl)pyrimidine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To 0.01 g (0.09 mmol) of 10% palladium on carbon was added a solution of 0.14 g (0.45 mmol) of the title compound from Step A in 5 mL anhydrous methanol. The resulting suspension was subjected to hydrogen at atmospheric pressure while stirring. After 4 h the mixture was filtered through a pad of Celite. The pad was washed with methanol (25 mL) and the combined filtrates were concentrated in vacuo to afford the title compound as a pale yellow residue without further purification. LC/MS: m/z (ES) 179.1 (MH)+.

Workup

  1. filtrationAfter 4 h the mixture was filtered through a pad of Celite
  2. washThe pad was washed with methanol (25 mL)
  3. concentrationthe combined filtrates were concentrated in vacuo

Sources & evidence

ORD record
ord-c03851bef3c544118340274da6b0aac3
Source dataset
uspto-grants-2013_01
Patent number
US08354403B2

Reaction notes

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