Sodium hydride → 1-(4-Pyridinylmethyl)-1H-pyrazol-3-amine

HRID 883051Notes

Reaction equation

HRID 883051 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][C:5]([N:8]2C(=O)C3C(=CC=CC=3)C2=O)=[N:4]1.Cl[CH2:20][C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1>CN(C=O)C>[N:24]1[CH:25]=[CH:26][C:21]([CH2:20][N:3]2[CH:7]=[CH:6][C:5]([NH2:8])=[N:4]2)=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 745714-(Chloromethyl)pyridineHCID 178514958HCID 178514958, compound

Product 1

HCID 470027731-(4-Pyridinylmethyl)-1H-pyrazol-3-amineYield 83%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

NaH (0.9 g., 60% suspension in liquid paraffin) is dissolved in DMF (10 ml) and 2-(1H-pyrazole-3-yl)-isoindole-1,3-dione (11.7 mmol) is added at 0° C. To this solution is added 4-chloromethyl-pyridine (11.7 mmol) and the mixture is heated to 50° C. for 16 hours. The solvent is removed in vacuo. The residue is dissolved in ethanol (100 ml) and hydrazinium-hydroxide (70 ml) is added and the mixture is heated to 120° C. for 9 days. The solvent is removed in vacuo. 1-Pyridine-4-ylmethyl-1H-pyrazole-3-ylamine is obtained after column chromatography as colorless oil in a yield of 83%; LC-MS (method B): 0.44 min, 175.15 (M+H+);

Workup

  1. customThe solvent is removed in vacuo
  2. dissolutionThe residue is dissolved in ethanol (100 ml)
  3. additionhydrazinium-hydroxide (70 ml) is added
  4. temperaturethe mixture is heated to 120° C. for 9 days
  5. customThe solvent is removed in vacuo

Sources & evidence

ORD record
ord-9e356fa9b0e948aaa35f32ce2954c18a
Source dataset
uspto-grants-2012_08
Patent number
US08236824B2

Reaction notes

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