Water → 2-(Cyclobutyloxy)-8-(methyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine
Reaction equation
Br[C:2]1[N:3]([CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][O:18]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH:13]1[CH2:16][CH2:15][CH2:14]1)[N:5]=2.C[O-].[Na+].[C:26](OCC)(=[O:28])C.O>CO>[CH:13]1([O:12][C:6]2[N:5]=[C:4]3[C:9]([N:10]=[C:2]([O:28][CH3:26])[N:3]3[CH:17]3[CH2:22][CH2:21][CH2:20][CH2:19][O:18]3)=[C:8]([NH2:11])[N:7]=2)[CH2:16][CH2:15][CH2:14]1Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 67 °C
Procedure
8-Bromo-2-(cyclobutyloxy)-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-amine (1.79 g, 4.86 mmol) was dissolved in anhydrous methanol (25 ml) and 25% sodium methoxide in methanol (2.274 ml, 9.72 mmol) was added under nitrogen. The mixture was heated at 67° C. for 24 hours and then cooled to room temperature. Ethyl acetate and water were added and the layers separated. The aqueous layer was extracted twice more with ethyl acetate, and the organic extracts were combined, washed with brine, dried over anhydrous magnesium sulfate, and evaporated to give the title compound as a cream foam (1.27 g).
Workup
- temperaturecooled to room temperature
- customthe layers separated
- extractionThe aqueous layer was extracted twice more with ethyl acetate
- washwashed with brine
- dry with materialdried over anhydrous magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-ba119a8bb7164e61bc264b0e500e11b2
- Source dataset
- uspto-grants-2016_05
- Patent number
- US09346806B2
Reaction notes
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