Morpholine → 2-Chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine

HRID 421306Notes

Reaction equation

HRID 421306 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[C:4](Cl)[N:3]=1.[NH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(O)C>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:11][CH:12]2[CH2:16][CH2:15][O:14][CH2:13]2)=[C:4]([N:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[N:3]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 593335962,6-Dichloro-9-(tetrahydrofuran-3-ylmethyl)-9H-purine

Product 1

HCID 593335062-Chloro-6-morpholin-4-yl-9-(tetrahydrofuran-3-ylmethyl)-9H-purine

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2,6-Dichloro-9-(tetrahydrofuran-3-ylmethyl)-9H-purine (41 g) was dissolved in ethanol (200 ml) followed by the addition of morpholine (20 ml) and the resulting mixture was heated to reflux for 2 hours. The solvent was evaporated under reduced pressure, the residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution, and the organic layer was washed with water and dried over magnesium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel chromatography (hexane:ethyl acetate, 5:5 to 2:8 to 0:10) to give the title compound (41 g) as a white solid.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 2 hours
  3. customThe solvent was evaporated under reduced pressure
  4. customthe residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution
  5. washthe organic layer was washed with water
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated under reduced pressure
  8. customthe residue was purified by silica gel chromatography (hexane:ethyl acetate, 5:5 to 2:8 to 0:10)

Sources & evidence

ORD record
ord-15f28acd93234464a79583052c66f7fb
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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