Hydrochloric Acid → 6-Amino-2-[(2-methylpropyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-7,9-dihydro-8H-purin-8-one
Reaction equation
Br[C:2]1[N:3]([CH2:17][CH:18]2[CH2:23][CH2:22][O:21][CH2:20][CH2:19]2)[C:4]2[C:9]([N:10]=1)=[C:8]([NH2:11])[N:7]=[C:6]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:5]=2.Cl.[OH-:25].[Na+]>C(O)CCC>[NH2:11][C:8]1[N:7]=[C:6]([O:12][CH2:13][CH:14]([CH3:16])[CH3:15])[N:5]=[C:4]2[C:9]=1[NH:10][C:2](=[O:25])[N:3]2[CH2:17][CH:18]1[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
8-Bromo-2-[(2-methylpropyl)oxy]-9-(tetrahydro-2H-pyran-4-ylmethyl)-9H-purin-6-amine (100 mg) in n-butanol (2 mL) was refluxed with concentrated hydrochloric acid (2 mL) at 100° C. (external temperature) for 3 hours. The reaction mixture was evaporated under reduced pressure to dryness. To the reaction mixture was then added a small volume of water and an equivalent volume of methanol to give a suspension, which was then neutralised to by the addition of 2M sodium hydroxide (from pH ˜3 to 7). This was then evaporated under reduced pressure to give a beige solid which was purified by C18 reverse phase chromatography using water (containing 0.1% formic acid)-acetonitrile (containing 0.05% formic acid) as eluent (20-60%). This gave the title compound (13 mg) as white solid.
Workup
- customThe reaction mixture was evaporated under reduced pressure to dryness
- additionTo the reaction mixture was then added a small volume of water
- customan equivalent volume of methanol to give a suspension, which
- customThis was then evaporated under reduced pressure
- customto give a beige solid which
- customwas purified by C18 reverse phase chromatography
Sources & evidence
- ORD record
- ord-33552fb8ff6e43a1a3ca5c7500b4b33d
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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