Phosphorus oxychloride → HCID 86678988, compound

Participants

Reaction Conditions

Reaction Steps

4-amino-5-cyclopropyl-6-oxo-2-[1-(3,3,4,4,4-pentafluorobutyl)-1H-pyrazolo[3,4-b]pyridin-3-yl]-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidine-5-carboxamide, as described in Example 162, (565 mg, 1.201 mmol) was taken up in pyridine (6 mL) and the solution cooled to 0° C. Phosphorous oxychloride (0.896 ml, 9.61 mmol) was then added dropwise and the reaction mixture was warmed to room temperature. After 15 minutes, the pyridine solvent was concentrated in vacuo and the residue taken up in EtOAc. The mixture was then washed with water, brine and dried over sodium sulfate. The residue was purified by silica gel column chromatography using a hexanes/EtOAc gradient to give the title compound, Chiral separation by SFC provided both enantiomers of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 9.07 (1H, d, J=8.07 Hz), 8.69 (1H, d, J=4.42 Hz), 7.44 (1H, dd, J=8.08, 4.48 Hz), 7.16 (2H, s), 4.93 (2H, t, J=6.82 Hz), 3.08-2.95 (2H, m), 1.80-1.73 (1H, m), 0.93-0.88 (1H, m), 0.65 (2H, d, J=8.31 Hz), 0.55-0.48 (1H, m). m/z=479.1 (M+H).

Provenance & Evidence