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

HRID 219712Notes

Reaction equation

HRID 219712 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[CH2:26][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[CH2:26][CH2:25]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 69026905Acetic acid 3-[4-(2-tert-butyl-6-cyclopropyl-pyrimidin-4-yl)-piperazin-1-yl]-propyl ester

Product 1

HCID 690296093-[4-(2-tert-Butyl-6-cyclopropyl-pyrimidin-4-yl)-piperazin-1-yl]-propan-1-olYield 30.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

3.7 g of acetic acid 3-[4-(2-tert-butyl-6-cyclopropyl-pyrimidin-4-yl)-piperazin-1-yl]-propyl ester (10.2 mmol) and 0.4 g of lithium hydroxide (16.7 mmol) were stirred overnight in 20 ml of tetrahydrofuran and 20 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 (0-8%) as eluent to yield 1.0 g of the title compound.

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-57f645df30404330a82ef0f3e30272c0
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

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