Cesium carbonate → 4-Chloro-5-((tetrahydrofuran-2-yl)methyl)-5H-pyrrolo[3,2-d]pyrimidine

To a suspension of 4-chloro-5H-pyrrolo[3,2-d]pyrimidine (150 mg) in N,N-dimethylformamide (1.0 mL) was added cesium carbonate (478 mg) under ice-cooling, and the mixture was stirred while warming to room temperature for 15 min. To the reaction mixture was added 2-(bromomethyl)tetrahydrofuran (242 mg), and the mixture was stirred at room temperature for 26 hrs. The reaction mixture was diluted with water (20 mL) and extracted with ethyl acetate (30 mL×3). The organic layer was washed with saturated brine (30 mL×3) and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was subjected to silica gel column chromatography (silica gel, eluent:hexane/ethyl acetate=90/10→20/80). The object fraction was concentrated under reduced pressure and dried to give the title compound (200 mg) as a colorless oil.

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 26 hrs
3. extractionextracted with ethyl acetate (30 mL×3)
4. washThe organic layer was washed with saturated brine (30 mL×3)
5. dry with materialdried over anhydrous magnesium sulfate
6. customThe solvent was evaporated under reduced pressure
7. concentrationThe object fraction was concentrated under reduced pressure
8. customdried

ORD record

ord-11141ae7736347c59f6cb0f9438656ed

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08178543B2