1H-Pyrazol-3-amine, 5-methyl- → (2-chloro-purin-4-yl)-(5-methyl-1H-pyrazol-3-yl)-amine

HRID 1743176Notes

Reaction equation

HRID 1743176 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:9](Cl)([N:10]=1)[N:8]=[CH:7][N:6]=2.[CH3:12][C:13]1[NH:17][N:16]=[C:15]([NH2:18])[CH:14]=1>C(O)C>[Cl:1][C:2]1[N:3]=[CH:4][C:5]2[C:9]([NH:18][C:15]3[CH:14]=[C:13]([CH3:12])[NH:17][N:16]=3)([N:10]=1)[N:8]=[CH:7][N:6]=2

Participants

4

Reactant 2

HCID 931461H-Pyrazol-3-amine, 5-methyl-HCID 219392112,4-Dichloro-purine

Product 1

HCID 21939154(2-chloro-purin-4-yl)-(5-methyl-1H-pyrazol-3-yl)-amineYield 58%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2,4-dichloro-purine (2.0 g, 10.6 mmol) in anhydrous ethanol (10 mL) was added 5-methyl-1H-pyrazol-3-yl amine (2.05 g, 21.2 mmol). The resulting mixture was stirred at room temperature for 48 h. The resulting precipitate was collected by filtration, washed with ethanol, and dried under vacuum to afford 1.524 g (58% yield) of (2-chloro-purin-4-yl)-(5-methyl-1H-pyrazol-3-yl)-amine which was used in the next step without further purification. To a solution of (2-chloro-purin-4-yl)-(5-methyl-1H-pyrazol-3-yl)-amine (200 mg, 0.80 mmol) was added 4-methylpiperidine (4 mL, 8.01 mmol) and the reaction mixture heated at reflux overnight. The solvent was evaporated and the residue dissolved in a mixture EtOH:water (1:3, 4 mL). Potassium carbonate (57 mg, 0.41 mmol) was added and the mixture was stirred at room temperature for 2 hours. The resulting suspension was filtered, washed with water (×2) and rinsed with Et2O (×2) to afford IV-33 as a white solid (225 mg, 90%): mp >300° C.;

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with ethanol
  3. customdried under vacuum

Sources & evidence

ORD record
ord-8a7412f6b56946d5ad37c8edab51b420
Source dataset
uspto-grants-2006_03
Patent number
US07008948B2

Reaction notes

Loading…