Lithium Hydroxide → 3-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-ol

HRID 219704Notes

Reaction equation

HRID 219704 reaction equation
[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:16][CH2:15][N:14]([CH2:17][CH2:18][CH2:19][O:20]C(=O)C)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Li+]>O1CCCC1.O>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][OH:20])[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:24]2[CH2:27][CH2:26][CH2:25]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69025431Acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propyl ester

Product 1

HCID 690262333-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-olYield 40.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

7 g of acetic acid 3-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-propyl ester (18.7 mmol) and 0.67 g of lithium hydroxide (28.0 mmol) were stirred overnight in a mixture of 40 ml of tetrahydrofuran and 40 ml of water. The reaction mixture was partitioned between water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and the solvent was evaporated. The crude product was purified by chromatography on silica gel using dichloromethane-methanol (2%) as eluent to yield 2.5 g of the title compound as an oil that crystallized upon standing.

Workup

  1. customThe reaction mixture was partitioned between water and ethyl acetate
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-0965dbf844454989ae6335d53734cf5e
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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