5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one → 5-(3-fluoro-4-(3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one

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Reaction Steps

A solution of 5-(3-fluoro-4-(1-(4-methoxybenzyl)-3-(4-(morpholine-4-carbonyl)phenyl)-1H-pyrazolo[3,4-b]pyridin-4-yloxy)phenyl)-3-methyl-2-(phenylamino)pyrimidin-4(3H)-one (0.014 g, 0.0190 mmol) in TFA (1 mL) was stirred at 60° C. for 3.5 hours. The reaction mixture was concentrated in vacuo to yield a crude yellow gum. The crude product was purified by flash column chromatography, eluting with 10:1 CH2Cl2/MeOH. The isolated product was then partitioned between EtOAc and saturated NaHCO3. The layers were separated and the aqueous layer was re-extracted with EtOAc. The combined EtOAc layers were dried over Na2SO4, filtered and concentrated to yield the desired product (6.9 mg; 59%) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 9.03 (br s, 1H), 8.40 (d, 1H), 8.09 (s, 1H), 8.08 (m, 2H), 7.86 (dd, 1H), 7.66 (m, 1H), 7.57-7.48 (m, 5H), 7.38 (m, 2H), 7.16 (m, 1H), 6.41 (d, 1H), 3.60 (m, 8H), 3.58 (s, 3H). LRMS (APCI pos) m/e 618 (M+1).

Provenance & Evidence