Hydrazine → 4-(4-Hydrazino-6-morpholin-4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol

HRID 249693Notes

Reaction equation

HRID 249693 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]([CH2:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[N:3]=1.[NH2:20][NH2:21]>O1CCOCC1>[NH:20]([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]([CH2:14][CH2:15][C:16]([CH3:19])([OH:18])[CH3:17])[N:3]=1)[NH2:21]

Participants

4

Reactant 2

HCID 9321HydrazineHCID 580857464-(4-Chloro-6-morpholin-4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol

Product 1

HCID 580857564-(4-Hydrazino-6-morpholin-4-yl-pyrimidin-2-yl)-2-methyl-butan-2-olYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

4-(4-chloro-6-morpholin-4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol (3.3 g, 11.5 mmol) was dissolved in dioxane (30 mL). To the reaction mixture was added anhydrous hydrazine (7.5 mL, 220 mmol). The reaction was then heated at reflux for five hours. The solvent was removed under reduced pressure, and the crude solid was dissolved in a mixture of dichloromethane (800 mL) and 10% potassium carbonate (40 mL). The organic layer was isolated, dried with sodium sulfate, and evaporated to give 4-(4-hydrazino-6-morpholin-4-yl-pyrimidin-2-yl)-2-methyl-butan-2-ol (2.61 g, 9.2 mmol).

Workup

  1. temperatureThe reaction was then heated
  2. temperatureat reflux for five hours
  3. customThe solvent was removed under reduced pressure
  4. dissolutionthe crude solid was dissolved in a mixture of dichloromethane (800 mL) and 10% potassium carbonate (40 mL)
  5. customThe organic layer was isolated
  6. dry with materialdried with sodium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-e96de8b757d1411e896b628a0d1b0fdd
Source dataset
uspto-grants-2011_01
Patent number
US07863270B2

Reaction notes

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