Water → tert-Butyl 4-(6-chloro-5-nitropyrimidin-4-yl)piperazine-1-carboxylate

HRID 2112895Notes

Reaction equation

HRID 2112895 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=1.[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(N(CC)CC)C.O>C(#N)C>[C:12]([O:16][C:17]([N:19]1[CH2:24][CH2:23][N:22]([C:2]2[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([Cl:11])[N:5]=[CH:4][N:3]=2)[CH2:21][CH2:20]1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 203124,6-Dichloro-5-nitropyrimidineHCID 143452tert-Butyl piperazine-1-carboxylate

Product 1

HCID 21477639tert-Butyl 4-(6-chloro-5-nitropyrimidin-4-yl)piperazine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4,6-Dichloro-5-nitropyrimidine [CAS No. 4316-93-2] (2.0 g) was dissolved in acetonitrile (30 mL), and then piperazine-1-carboxylic acid t-butyl ester (1.92 g) and triethylamine (2.1 mL) were added to this solution. The reaction solution was stirred at room temperature for 14 hours, and then water (30 mL) was added. The reaction solution was stirred at room temperature for 30 minutes, and then the precipitate was collected by filtration. The obtained solid was washed with water and hexane to give the title compound (2.94 g).

Workup

  1. stirringThe reaction solution was stirred at room temperature for 30 minutes
  2. filtrationthe precipitate was collected by filtration
  3. washThe obtained solid was washed with water and hexane

Sources & evidence

ORD record
ord-dde78d0f2ba34eb5be44adc5a029b910
Source dataset
uspto-grants-2009_04
Patent number
US07524847B2

Reaction notes

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