Water → 2-Chloro-4-hydrazinylpyrimidine

HRID 601004Notes

Reaction equation

HRID 601004 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.C(N(CC)CC)C.[NH2:16][NH2:17].O>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:16][NH2:17])[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 9321HydrazineHCID 775312,4-Dichloropyrimidine

Product 1

HCID 160921982-Chloro-4-hydrazinylpyrimidineYield 23%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloropyrimidine (1.49 g, 10.0 mmol) in ethanol (25 mL) was added triethylamine (2.02 g, 2.78 mL, 20.0 mmol) and hydrazine (321 mg, 0.321 mL, 10.0 mmol). The mixture was stirred at room temperature for 2 h. Water was added and the mixture was extracted with dichloromethane. The organic layer was dried over MgSO4, concentrated. The residue was purified by silica gel column chromatograghy eluted with methanol:dichloromethane (2 to 5% methanol) to give (2-chloro-pyrimidin-4-yl)-hydrazine (330 mg, 23%) as a white solid. MS (ES+): m/z=144.9.

Workup

  1. extractionthe mixture was extracted with dichloromethane
  2. dry with materialThe organic layer was dried over MgSO4
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel column chromatograghy
  5. washeluted with methanol

Sources & evidence

ORD record
ord-f97b039f0edf4fbd92c86121064356ce
Source dataset
uspto-grants-2011_03
Patent number
US07902239B2

Reaction notes

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