Dimethylformamide → 2-chloro-6-morpholin-4-yl-9-(tetrahydropyran-2-yl)-9H-purine-8-carbaldehyde

温度

-78 °C

To a solution of 4-(2-chloro-9-(tetrahydro-2H-pyran-2-yl)-9H-purin-6-yl)morpholine (1.96 g, 6.05 mmol) in THF (75 mL) was a 2.5 M solution of n-BuLi in hexanes (3.2 mL, 7.9 mmol) at −78° C. The reaction mixture was then stirred at −78° C. for 45 minutes. DMF (0.94 mL, 12.1 mmol) was then added. The resulting mixture was stirred at −78° C. for 2 hours before being poured slowly onto ice. The mixture was then extracted three times with DCM. The combined extracts were washed with water, dried over sodium sulfate and concentrated. The crude product was purified by flash chromatography (25% EtOAc in heptane) to give the title compound (1.1 g, 52%). LCMS: M+H+=352.2.

1. customat −78° C
2. stirringThe resulting mixture was stirred at −78° C. for 2 hours
3. additionbefore being poured slowly onto ice
4. extractionThe mixture was then extracted three times with DCM
5. washThe combined extracts were washed with water
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. customThe crude product was purified by flash chromatography (25% EtOAc in heptane)

ORDレコード

ord-e94d3b798b994686aeaffefe6aaaee63

出典データセット

uspto-grants-2012_04

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US08158625B2