Morpholine → HCID 59333625, compound

HRID 1876523Notes

Reaction equation

HRID 1876523 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[C@H:17]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]2)=[C:10](Cl)[N:9]=1>C(O)C>[Cl:7][C:8]1[N:16]=[C:15]2[C:11]([N:12]=[CH:13][N:14]2[C@H:17]2[CH2:21][CH2:20][N:19]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[CH2:18]2)=[C:10]([N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:9]=1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 59333649HCID 59333649, compound

Product 1

HCID 59333625HCID 59333625, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

Morpholine (0.8 ml) and ethanol (10 ml) were added to tert-butyl (3S)-3-(2,6-dichloro-9H-purin-9-yl)pyrrolidine-1-carboxylate (1.55 g, 4.3 mmol) and the resulting mixture was stirred at 80° C. for 2 hours. The reaction mixture was cooled and then the solvent was evaporated under reduced pressure. The residue was partitioned with ethyl acetate and saturated aqueous sodium bicarbonate solution, the organic layer was dried over magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound (1.76 g, 100%) as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent was evaporated under reduced pressure
  3. customThe residue 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

Sources & evidence

ORD record
ord-ad608350e4914ce8b507cb78d9354188
Source dataset
uspto-grants-2012_11
Patent number
US08309546B2

Reaction notes

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