4-(5-Nitro-pyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester → 1,1-Dimethylethyl 4-(5-amino-2-pyrimidinyl)-1-piperazinecarboxylate

HRID 557722Notes

Reaction equation

HRID 557722 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14]2[N:19]=[CH:18][C:17]([N+:20]([O-])=O)=[CH:16][N:15]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>O1CCCC1.CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([C:14]2[N:19]=[CH:18][C:17]([NH2:20])=[CH:16][N:15]=2)[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 667385574-(5-Nitro-pyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester

Product 1

HCID 594643191,1-Dimethylethyl 4-(5-amino-2-pyrimidinyl)-1-piperazinecarboxylate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-(5-nitro-pyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester (927 mg, 3 mmol, prepared from 2-chloro-5-nitropyrimidine and N-Boc-piperazine) in tetrahydrofuran (20 mL) and methanol (30 mL) was added 10% palladium on carbon (240 mg) and the mixture was hydrogenated at 50 psi for 1 hr. The mixture was filtered and the solvents were evaporated. The residue was dried in vacuum to give 4-(5-amino-pyrimidin-2-yl)-piperazine-1-carboxylic acid tert-butyl ester.

Workup

  1. filtrationThe mixture was filtered
  2. customthe solvents were evaporated
  3. customThe residue was dried in vacuum

Sources & evidence

ORD record
ord-6702fb79851248e9a2eb4117e62ca430
Source dataset
uspto-grants-2011_11
Patent number
US08058299B2

Reaction notes

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