Ethanol → 1-(6-Hydrazinopyrimidin-4-yl)azetidin-3-ol

HRID 242241Notes

Reaction equation

HRID 242241 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:3]=1.O.[NH2:14][NH2:15].C(O)C>C1COCC1>[NH:14]([C:2]1[N:7]=[CH:6][N:5]=[C:4]([N:8]2[CH2:11][CH:10]([OH:12])[CH2:9]2)[CH:3]=1)[NH2:15]

Participants

5

Reactant 3

HCID 702EthanolHCID 24654Hydrazine hydrate (1:1)HCID 579250791-(6-Chloropyrimidin-4-yl)azetidin-3-ol

Product 1

HCID 552790421-(6-Hydrazinopyrimidin-4-yl)azetidin-3-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

960 mg (5.2 mmol) 1-(6-chloropyrimidin-4-yl)azetidin-3-ol and 2.5 ml (51.7 mmol) hydrazine hydrate are initially introduced into a mixture of 10 ml ethanol and 10 ml THF. The reaction is carried out at 130° C. for 1 h in a single mode microwave (CEM Explorer). The mixture is concentrated to approx. 20-50% of the original volume of liquid and is left to stand at RT for 48 h. The supernatant is decanted off from the solid formed and the solid is washed three times with 1.5 ml cold ethanol each time. It is dried under a high vacuum.

Workup

  1. concentrationThe mixture is concentrated to approx. 20-50% of the original volume of liquid
  2. waitis left
  3. waitto stand at RT for 48 h
  4. customThe supernatant is decanted off from the solid
  5. customformed
  6. washthe solid is washed three times with 1.5 ml cold ethanol each time
  7. customIt is dried under a high vacuum

Sources & evidence

ORD record
ord-74284d8763534535827587612fc912d9
Source dataset
uspto-grants-2014_02
Patent number
US08653111B2

Reaction notes

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