Ammonia → HCID 86678986, compound

Participants

Reaction Steps

A 2 M solution of ammonia in MeOH (28.6 mL, 57.3 mmol) was added to ethyl 4-amino-5-methyl-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-carboxylate, as prepared by the procedure described in Example 158, (220 mg, 0.441 mmol) and the resultant mixture heated at 50° C. for 16 hours. The reaction mixture was concentrated in vacuo and the residue purified by silica gel column chromatography using a DCM/MeOH (with 0.5% NH4OH) gradient. Chiral separation by SFC using a Chiralpak AD column provided both enantiomers of the title compound. 1H NMR (500 MHz, DMSO-d6): δ 11.27 (1H, s), 9.02 (1H, dd, J=8.06, 1.62 Hz), 8.64 (1H, dd, J=4.50, 1.63 Hz), 7.45 (1H, s), 7.38 (1H, dd, J=8.07, 4.49 Hz), 7.19 (1H, s), 6.82 (2H, s), 4.88 (2H, t, J=6.80 Hz), 3.04-2.90 (2H, m), 1.57 (3H, s). m/z=471.1 (M+H).

Provenance & Evidence