Hydrochloric Acid → 6-Amino-2-{[(1S)-1-methylbutyl]oxy}-9-[2-(3-piperidinyl)ethyl]-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:24]C)[N:13]2[CH2:16][CH2:17][CH:18]2[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]2)=[C:9]([NH2:26])[N:8]=1)[CH2:3][CH2:4][CH3:5].Cl.O1CCOCC1>CO>[NH2:26][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:24])[N:13]2[CH2:16][CH2:17][CH:18]1[CH2:23][CH2:22][CH2:21][NH:20][CH2:19]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 2-{[(1S)-1-methylbutyl]oxy}-8-(methyloxy)-9-[2-(3-piperidinyl)ethyl]-9H-purin-6-amine (35 mg, 0.097 mmol) in methanol (4 ml) was added 4M HCl in dioxane (1.5 ml, 6.00 mmol) and the mixture was allowed to stir at room temperature for 1.5 hours. The reaction was then dried under a stream of nitrogen in the Radleys blowdown apparatus to give the crude product. This was redissolved in methanol (˜5 mL) and passed down a 2 g aminopropyl (—NH2) SPE cartridge. The filtrate was dried under a stream of nitrogen in Radleys blowdown apparatus. The sample was dissolved in 1:1 MeOH:DMSO (1 ml) and purified by Mass Directed AutoPrep (Method A). The solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus to give the title compound as an off-white solid (21.5 mg).
Workup
- customThe reaction was then dried under a stream of nitrogen in the Radleys blowdown apparatus
- customto give the crude product
- customThe filtrate was dried under a stream of nitrogen in Radleys blowdown apparatus
- dissolutionThe sample was dissolved in 1:1 MeOH
- customDMSO (1 ml) and purified by Mass Directed AutoPrep (Method A)
- customThe solvent was dried under a stream of nitrogen in the Radleys blowdown apparatus
Sources & evidence
- ORD record
- ord-11a0ecf809ab4520af9028865a61e4b8
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08802684B2
Reaction notes
Loading…