Hydrazine → (6-Chloro-2-methoxy-pyrimidin-4-yl)hydrazine

HRID 2063605Notes

Reaction equation

HRID 2063605 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6](Cl)[N:5]=[C:4]([O:9][CH3:10])[N:3]=1.[NH2:11][NH2:12].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[Cl:1][C:2]1[N:3]=[C:4]([O:9][CH3:10])[N:5]=[C:6]([NH:11][NH2:12])[CH:7]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 11430Potassium CarbonateHCID 120521604,6-Dichloro-2-methoxypyrimidine

Product 1

HCID 55281294(6-Chloro-2-methoxy-pyrimidin-4-yl)hydrazineYield 39%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4,6-dichloro-2-methoxy-pyrimidine (1.1 g, 6.2 mmol) was dissolved in 100 mL of anhydrous tetrahydrofuran. To the resultant reaction solution hydrazine (0.19 mL, 6.2 mmol) and potassium carbonate (2.6 g, 18 mmol) were added and the reaction mixture was stirred for 3 days. The potassium carbonate was removed by filtration and the filtrate was concentrated in vacuo. Crystallization of the residue from ethyl acetate:hexanes yielded 414 mg (39%) of the title compound.

Workup

  1. additionwere added
  2. customThe potassium carbonate was removed by filtration
  3. concentrationthe filtrate was concentrated in vacuo
  4. customCrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-3e3c546c341f4ad883e8e834fd124bcf
Source dataset
uspto-grants-2012_10
Patent number
US08288398B2

Reaction notes

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