Morpholine → 6-Morpholin-4-yl-9-(tetrahydro-2H-pyran-2-yl)-2-(tributylstannyl)-9H-purine

HRID 421313Notes

Reaction equation

HRID 421313 reaction equation
Cl[C:2]1[N:10]=[C:9]([Sn:11]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]2[C:3]=1[N:4]=[CH:5][N:6]2[CH:24]1[CH2:29][CH2:28][CH2:27][CH2:26][O:25]1.[NH:30]1[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1>C(#N)C>[N:30]1([C:2]2[N:10]=[C:9]([Sn:11]([CH2:20][CH2:21][CH2:22][CH3:23])([CH2:16][CH2:17][CH2:18][CH3:19])[CH2:12][CH2:13][CH2:14][CH3:15])[N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][N:6]3[CH:24]2[CH2:29][CH2:28][CH2:27][CH2:26][O:25]2)[CH2:35][CH2:34][O:33][CH2:32][CH2:31]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 112263006-Chloro-9-(tetrahydro-2H-pyran-2-yl)-2-(tributylstannyl)-9H-purine

Product 1

HCID 593336046-Morpholin-4-yl-9-(tetrahydro-2H-pyran-2-yl)-2-(tributylstannyl)-9H-purineYield 91.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6-Chloro-9-(tetrahydro-2H-pyran-2-yl)-2-(tributylstannyl)-9H-purine (3.3 g, 6.25 mmol) was dissolved in acetonitrile (30 ml) followed by the addition of morpholine (2.2 ml, 25 mmol) and the resulting mixture was heated to reflux for 1 hour. The reaction mixture was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution, the organic layer was dried over magnesium sulfate, and then the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1 to 8:2) to give the title compound (3.3 g, 91%) as a pale yellow oil.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureto reflux for 1 hour
  3. customThe reaction mixture was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution
  4. dry with materialthe organic layer was dried over magnesium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel chromatography (hexane:ethyl acetate=9:1 to 8:2)

Sources & evidence

ORD record
ord-ed798535387844c58392e0b09e6fc0e4
Source dataset
uspto-grants-2012_01
Patent number
US08097622B2

Reaction notes

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