Hydrazine → 4-[2-(4-Hydrazino-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine

HRID 249688Notes

Reaction equation

HRID 249688 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1.[NH2:23][NH2:24]>O1CCOCC1>[NH:23]([C:2]1[CH:7]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[N:5]=[C:4]([O:14][CH2:15][CH2:16][N:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)[N:3]=1)[NH2:24]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 580857604-[2-(4-Chloro-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine

Product 1

HCID 580857314-[2-(4-Hydrazino-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholineYield 102.8%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-[2-(4-Chloro-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine (2.0 g; 6 mmol) was dissolved in dioxane (100 mL) and hydrazine (2 mL; 60 mmol) was added. The solution was heated to reflux for one hour, at which point the solvent was evaporated. The solid was dissolved in dichloromethane (100 mL) and washed with 10% sodium carbonate (10 mL). The organic layer was dried over magnesium sulfate and evaporated to give 4-[2-(4-Hydrazino-6-(morpholin-4-yl)-pyrimidin-2-yloxy)-ethyl]-morpholine (2.0 g)

Workup

  1. temperatureThe solution was heated
  2. temperatureto reflux for one hour, at which point the solvent
  3. customwas evaporated
  4. dissolutionThe solid was dissolved in dichloromethane (100 mL)
  5. washwashed with 10% sodium carbonate (10 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-bd65a433e07543e7b19dceef0ae3205d
Source dataset
uspto-grants-2011_01
Patent number
US07863270B2

Reaction notes

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