Morpholine → 4-(2-chloro-9H-purin-6-yl)morpholine

HRID 2218205Notes

Reaction equation

HRID 2218205 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4](Cl)[N:3]=1.[NH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1>O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][NH:8]2)=[C:4]([N:12]2[CH2:17][CH2:16][O:15][CH2:14][CH2:13]2)[N:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 53244122,6-Dichloropurine

Product 1

HCID 32746034-(2-chloro-9H-purin-6-yl)morpholineYield 96%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

As shown in Scheme 3 above, a mixture of 2,6-dichloropurine (1.90 g, 10 mmol) and morpholine (2.34 g, 30 mmol) in water (25 mL) was heated under reflux for 15 min. Solidified reaction mixture was cooled to room temperature. Solid was filtered out and washed with water, methanol and ether. The 2-chloro-6-morpholin-4-yl-9H-purine was obtained in 96% yield (2.30 g). A mixture of 2-chloro-6-morpholin-4-yl-9H-purine (1.92 g, 8 mmol) and 2-(3,4-dimethoxyphenyl)ethylamine (4.35 g, 24 mmol) in sealed tube and under nitrogen was stirred at 190-195° C. for 1 hour. The reaction mixture turned to clear solution initially and then formed a slurry. The reaction mixture was cooled to room temperature diluted with methanol (8 mL) and the solid was collected by filtration, washed with methanol and Et2O and dried to afford 2.30 g (74% yield) of [2-(3,4-dimethoxy-phenyl)-ethyl]-(6-morpholin-4-yl-9H-purin-2-yl)amine.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 15 min
  3. filtrationSolid was filtered out
  4. washwashed with water, methanol and ether

Sources & evidence

ORD record
ord-7a9d869b787b41e68512c464539d8c0f
Source dataset
uspto-grants-2008_08
Patent number
US07410990B2

Reaction notes

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