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

HRID 1244758Notes

Reaction equation

HRID 1244758 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-6cc50b640c0a43bdac5ca81535dc4cbc
Source dataset
uspto-grants-2006_10
Patent number
US07122665B2

Reaction notes

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