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

HRID 989032Notes

Reaction equation

HRID 989032 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 (x2) and rinsed with Et2O(x2) to afford IV-33 as a white solid (225 mg, 90%): mp >300° C.; 1H NMR (DMSO) δ0.91 (3H, d), 1.10 (2H, m), 1.65 (3H, m), 2.24 (3H, s), 2.84 (2H, m), 4.60 (2H, m), 6.40 (1H, s), 7.87 (1H, m), 9.37-9.59 (1H, m), 12.03-12.39 (2H, m); IR (solid) 1651, 1612, 1574, 1484, 1446, 1327, 1317, 1255, 1203; MS 313.3 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-fd930f3b98824b74a536b00a38e9031c
Source dataset
uspto-grants-2003_10
Patent number
US06638926B2

Reaction notes

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