Dimethylformamide → 2-Butoxy-8-methoxy-9-(tetrahydrofuran-3-ylmethyl)-9H-purin-6-amine
Reaction equation
F[C:2](F)(F)[C:3](O)=O.C(N[C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[NH:19]2)=[C:15]([NH2:24])[N:14]=1)CCC.[C:25](=[O:28])([O-])[O-].[K+].[K+].CS(O[CH2:36][CH:37]1[CH2:41][CH2:40][O:39][CH2:38]1)(=O)=O.[CH3:42]N(C)C=O>>[CH2:25]([O:28][C:13]1[N:21]=[C:20]2[C:16]([N:17]=[C:18]([O:22][CH3:23])[N:19]2[CH2:36][CH:37]2[CH2:41][CH2:40][O:39][CH2:38]2)=[C:15]([NH2:24])[N:14]=1)[CH2:42][CH2:2][CH3:3]Participants
Conditions
- Temperature
- 60 °C
Procedure
A stirring mixture of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (3.25 gm) and potassium carbonate (3.83 gm) in dry N,N-dimethylformamide (30 ml) was heated with stirring at 60° C. for 1 h. Tetrahydro-3-furanylmethyl methanesulfonate (2 gm, Isomer 2) was added and the stirring mixture heated at 90° C. for 3 h. The solvent was evaporated, water was added and the mixture extracted three times with ethyl acetate. The combined extracts were washed with water then brine, dried by passing through a hydrophobic frit and stripped to give an orange solid. This was purified by C18 reverse phase chromatography using water (0.1% formic acid)-acetonitrile (0.05% formic acid) as eluent (20-60%) and the appropriate fractions combined and evaporated to give the title compound as a light orange solid, yield 2.2 gm.
Workup
- temperaturewas heated
- temperaturethe stirring mixture heated at 90° C. for 3 h
- customThe solvent was evaporated
- additionwater was added
- extractionthe mixture extracted three times with ethyl acetate
- washThe combined extracts were washed with water
- dry with materialbrine, dried
- customto give an orange solid
- customThis was purified by C18 reverse phase chromatography
- customevaporated
Sources & evidence
- ORD record
- ord-0041124f78164bf3af8c58033bf14dad
- Source dataset
- uspto-grants-2011_07
- Patent number
- US07977344B2
Reaction notes
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