Sodium Bicarbonate → 4-(3-fluoroazetidin-1-yl)-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine

Participants

Reaction Steps

4-Chloro-3-iodo-1-methyl-1H-pyrazolo[3,4-d]pyrimidine (C9) (2.00 g, 6.79 mmol), 3-fluoroazetidine (833 mg, 7.46 mmol), saturated aqueous sodium bicarbonate solution (30 mL), and tetrahydrofuran (40 mL) were combined and allowed to stir at room temperature for 18 hours. After removal of volatiles in vacuo, the residue was diluted with water. Filtration provided the product as a tan solid. Yield: 1.91 g, 5.73 mmol, 84%. LCMS m/z 334.0 (M+1). 1H NMR (400 MHz, DMSO-d6) δ 3.91 (s, 3H), 4.47-4.63 (m, 2H), 4.75-4.90 (m, 2H), 5.44-5.64 (m, 1H, JHF=58.0 Hz), 8.31 (s, 1H).

Provenance & Evidence