Water → N2-Butyl-8-methoxy-9-[2-(tetrahydro-2H-pyran-3-yl)ethyl]-9H-purine-2,6-diamine

Temperature

60 °C

A stirring mixture of N2-butyl-8-methoxy-9H-purine-2,6-diamine trifluoroacetic acid salt (200 mg) and potassium carbonate (236 mg) in dry N,N-dimethylformamide (2 ml) was heated with stirring at 60° C. for 1 h. 2-(Tetrahydro-2H-pyran-3-yl)ethyl methanesulfonate (142 mg) was added and the stirring mixture heated at 60° C. for 3 h. 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 phase separation cartridge and stripped to give a brown oil. 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 remove acetonitrile. The remaining aqueous mixture was made basic with saturated sodium hydrogen carbonate, extracted three times with dichloromethane and the combined extracts dried by passing through a phase separation cartridge then evaporated to afford the title compound as a brown solid, yield 138 mg.

1. temperaturewas heated
2. temperaturethe stirring mixture heated at 60° C. for 3 h
3. extractionthe mixture extracted three times with ethyl acetate
4. washThe combined extracts were washed with water
5. dry with materialbrine, dried
6. customby passing through a phase separation cartridge
7. customto give a brown oil
8. customThis was purified by C18 reverse phase chromatography
9. customevaporated
10. customto remove acetonitrile
11. extractionextracted three times with dichloromethane
12. customthe combined extracts dried
13. customby passing through a phase separation cartridge
14. customthen evaporated

ORD record

ord-37107d3f0b5144e8b5900a43d2a7a0d5

Source dataset

uspto-grants-2011_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07977344B2