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

HRID 2384509Notes

Reaction equation

HRID 2384509 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-e34941a59c1249acb4fca3d7270ec8ab
Source dataset
uspto-grants-2012_09
Patent number
US08263764B2

Reaction notes

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