Hydrazine hydrate (1:1) → 4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)piperazin-1-yl]-butylamine

HRID 219699Notes

Reaction equation

HRID 219699 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][CH2:20][N:21]3C(=O)C4C(=CC=CC=4)C3=O)[CH2:13][CH2:12]2)[CH:8]=[C:7]([CH:32]2[CH2:35][CH2:34][CH2:33]2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].O.NN>C(O)C>[C:1]([C:5]1[N:10]=[C:9]([N:11]2[CH2:12][CH2:13][N:14]([CH2:17][CH2:18][CH2:19][CH2:20][NH2:21])[CH2:15][CH2:16]2)[CH:8]=[C:7]([CH:32]2[CH2:35][CH2:34][CH2:33]2)[N:6]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 690260812-{4-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-isoindole-1,3-dione

Product 1

HCID 690260674-[4-(2-tert-Butyl-6-cyclobutyl-pyrimidin-4-yl)piperazin-1-yl]-butylamineYield 68.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.4 g of 2-{4-[4-(2-tert-butyl-6-cyclobutyl-pyrimidin-4-yl)-piperazin-1-yl]-butyl}-isoindole-1,3-dione (5.05 mmol) and 1.0 g of hydrazine hydrate (20.2 mmol) were dissolved in 20 ml of ethanol and heated to reflux for 1 h. The precipitate was filtered and the filtrate extracted with water and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to dryness to yield 1.2 g of the title compound.

Workup

  1. temperatureheated
  2. temperatureto reflux for 1 h
  3. filtrationThe precipitate was filtered
  4. extractionthe filtrate extracted with water and ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-53e301ff681744bb85772887fb338a00
Source dataset
uspto-grants-2012_06
Patent number
US08202868B2

Reaction notes

Loading…