2,2,2-Trifluoroethanol → 2-(2,2,2-Trifluoro-ethoxy)-6,7-dihydro-5H-pyrrolo[3,4-D]pyrimidine

To a solution of the tert-butyl 2-(methylsulfonyl)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (300 mg) in dry acetonitrile (20 mL), 2,2,2-trifluoroethanol (1.8 mL) and cesium carbonate (815 mg) were added. The resulting mixture was stirred at room temperature for 1 h. The precipitate was removed by filtration. The solution was evaporated, and the resulting residue was purified on a Biotage Horizon® system (silica, gradient 35-65% ethyl acetate in hexanes). After concentration, tert-butyl 2-(2,2,2-trifluoroethoxy)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate was treated with HCl (4M in methanol) for 1 h. The residue was passed through an ion exchange resin (Strata-X-C™) and eluted with methanol containing 10% ammonium hydroxide to yield 2-(2,2,2-trifluoroethoxy)-6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine as the title compound. LC/MS 220.0 (M+1).

1. customThe precipitate was removed by filtration
2. customThe solution was evaporated
3. customthe resulting residue was purified on a Biotage Horizon® system (silica, gradient 35-65% ethyl acetate in hexanes)
4. concentrationAfter concentration, tert-butyl 2-(2,2,2-trifluoroethoxy)-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate
5. additionwas treated with HCl (4M in methanol) for 1 h
6. washeluted with methanol containing 10% ammonium hydroxide

ORD record

ord-901f8a2b0673406abe431ce47f1821c6

Source dataset

uspto-grants-2011_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07906649B2