Hydrochloric Acid → 6-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[4-(tetrahydro-2H-pyran-4-ylamino)butyl]-7,9-dihydro-8H-purin-8-one
Reaction equation
[CH3:1][C@H:2]([O:6][C:7]1[N:15]=[C:14]2[C:10]([N:11]=[C:12]([O:27]C)[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]2[CH2:26][CH2:25][O:24][CH2:23][CH2:22]2)=[C:9]([NH2:29])[N:8]=1)[CH2:3][CH2:4][CH3:5].Cl.O1CCOCC1>CO>[NH2:29][C:9]1[N:8]=[C:7]([O:6][C@@H:2]([CH3:1])[CH2:3][CH2:4][CH3:5])[N:15]=[C:14]2[C:10]=1[NH:11][C:12](=[O:27])[N:13]2[CH2:16][CH2:17][CH2:18][CH2:19][NH:20][CH:21]1[CH2:26][CH2:25][O:24][CH2:23][CH2:22]1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
2-{[(1S)-1-Methylbutyl]oxy}-8-(methyloxy)-9-[4-(tetrahydro-2H-pyran-4-ylamino)butyl]-9H-purin-6-amine (30.35 mg, 0.075 mmol) was dissolved in methanol (2.0 ml) and treated with 4M HCl in 1,4 dioxane (0.467 ml, 1.866 mmol) and stirred in a capped vial over the weekend. The solvent was evaporated under nitrogen and the residue was dissolved in methanol and passed down an aminopropyl SPE cartridge (2 g, pre-conditioned with 2 column volumes of methanol) and washed through with 1 column volume of methanol. The eluant was evaporated under nitrogen in a blowdown unit to give the title compound as an off-white solid (28.34 mg).
Workup
- customThe solvent was evaporated under nitrogen
- dissolutionthe residue was dissolved in methanol
- washwashed through with 1 column volume of methanol
- customThe eluant was evaporated under nitrogen in a blowdown unit
Sources & evidence
- ORD record
- ord-edd61e910a19472580e59bd8337e67b7
- Source dataset
- uspto-grants-2013_11
- Patent number
- US08575181B2
Reaction notes
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