Cesium carbonate → Pf-04447943

Participants

Reaction Conditions

Reaction Steps

To a solution of 6-[(3S,4S)-4-methylpyrrolidin-3-yl]-1-(tetrahydro-2H-pyran-4-yl)-1H-pyrazolo[3,4-d]pyrimidin-4(5H)-one hydrogen chloride (7.75 g) (see preparation in step (a) of Example 73) in dimethylformamide (115 mL) was added iron triflate (900 mg), 2-(chloromethyl)pyrimidine hydrogen chloride (4.5 g), and cesium carbonate (22.2 g) and the reaction mixture was heated at 60° C. for 24 h. The reaction mixture was concentrated onto silica gel and purified by flash chromatography eluting with 0-15% methanoylethyl acetate/1% saturated ammonium hydroxide to provide the title compound (6 g). 400 MHz 1H NMR (CDCl3) δ 12.30 (brs, 1H), 8.63 (d, J=5.0, Hz, 2H), 8.03 (s, 1H). 7.20 (d, J=5.0, Hz, 1H), 4.84-4.79 (m, 1H), 4.30-4.27 (m, 1H), 4.14-4.08 (m, 2H), 3.87-3.82 (m, 1H), 3.63-3.55 (m, 2H), 3.47 (t, J=7.9 Hz, 1H), 3.29 (d, J=9.9 Hz, 1H), 2.88-2.86 (m, 1H), 2.60-2.56 (m, 1H), 2.46-2.24 (m, 4H), 1.93-1.84 (m, 2H), 1.24 (t, J=7.1 Hz, 3H). MS: (M+H m/z 396.2).

Provenance & Evidence