Hydrochloric Acid → 6-Amino-2-(butylamino)-9-[4-(tetrahydro-2-furanyl)butyl]-7,9-dihydro-8H-Purin-8-one
Reaction equation
[CH2:1]([NH:5][C:6]1[N:14]=[C:13]2[C:9]([N:10]=[C:11]([O:24]C)[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]2[CH2:23][CH2:22][CH2:21][O:20]2)=[C:8]([NH2:26])[N:7]=1)[CH2:2][CH2:3][CH3:4].Cl.O1CCOCC1>CO>[NH2:26][C:8]1[N:7]=[C:6]([NH:5][CH2:1][CH2:2][CH2:3][CH3:4])[N:14]=[C:13]2[C:9]=1[NH:10][C:11](=[O:24])[N:12]2[CH2:15][CH2:16][CH2:17][CH2:18][CH:19]1[CH2:23][CH2:22][CH2:21][O:20]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N2-butyl-8-(methyloxy)-9-[4-(tetrahydro-2-furanyl)butyl]-9H-purine-2,6-diamine (75 mg, 0.207 mmol) in methanol (10 ml) at room temperature was added 4M HCl in 1,4-dioxane (1.324 ml, 5.30 mmol) to give a pale straw coloured solution. The reaction mixture was stirred at ambient temperature overnight (16 hours) when LCMS showed the reaction had not proceeded to completion. The solvent was removed overnight (16 hours) using a nitrogen blowdown unit when LCMS confirmed the presence of the desired product. This crude product was loaded in methanol onto a 5 g aminopropyl SPE cartridge and eluted with methanol over 20 mins. The appropriate fractions were combined and evaporated under a stream of nitrogen to give the title compound as a white powder (49 mg).
Workup
- customto give a pale straw coloured solution
- customThe solvent was removed overnight (16 hours)
- washeluted with methanol over 20 mins
- customevaporated under a stream of nitrogen
Sources & evidence
- ORD record
- ord-a15c6d80de114c8a8c9ed12e5d2938c4
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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