Hydrazine hydrate (1:1) → Ammonia

HRID 20271

Reaction equation

HRID 20271 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][CH2:8][C:9]([O:11]CC)=O.O.[NH2:15][NH2:16]>C(O)(C)C>[NH3:1].[N:1]1[CH:6]=[CH:5][CH:4]=[N:3][C:2]=1[O:7][CH2:8][C:9]([NH:15][NH2:16])=[O:11]

Participants

5

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 22396258Ethyl 2-pyrimidinyloxyacetate

Product 2

HCID 222AmmoniaHCID 593475352-(Pyrimidin-2-yloxy)acetohydrazide

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of ethyl 2-pyrimidinyloxyacetate (GB2373186, step i ex 368) (4.4 g, 24.15 mmol) and hydrazine hydrate (5 mL, 160 mmol) in isopropanol (30 mL) was heated under reflux for 1 hour. The mixture was then cooled and concentrated under reduced pressure and the residue was purified by column chromatography on silica gel using dichloromethane:methanol:0.88 ammonia (100:0:0 to 100:10:1) to provide the title compound, 600 mg.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1 hour
  3. temperatureThe mixture was then cooled
  4. concentrationconcentrated under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-acc3963df842493485c6c9e822535ce0
Source dataset
uspto-grants-2010_06
Patent number
US07745630B2

Linked notes

Loading…