5-bromo-1-methyl-3-(pyrimidin-4-ylamino)pyridin-2(1H)-one → 5-tert-Butyl-2-(2-(hydroxymethyl)-3-(1-methyl-6-oxo-5-(pyrimidin-4-ylamino)-1,6-dihydropyridin-3-yl)phenyl)isoindolin-1-one

Participants

Reaction Steps

Using the same general procedure as in Example 105, reaction of 107a (250 mg, 0.889 mmol) with 103f (495 mg, 1.07 mmol) afforded 107 in 38% yield (166 mg) as an amorphous off-white solid: mp 216-218° C.; 1H NMR (500 MHz, DMSO-d6) δ 9.18 (s, 1H), 8.72 (d, J=2.0 Hz, 1H), 8.65 (s, 1H), 8.30 (d, J=5.5 Hz, 1H), 7.73 (d, J=8.5 Hz, 2H), 7.62 (dd, J=8.0, 1.5 Hz, 1H), 7.54 (d, J=2.0 Hz, 1H), 7.51 (t, J=7.5 Hz, 1H), 7.46 (dd, J=7.5, 1.0 Hz, 1H), 7.40 (dd, J=7.5, 1.5 Hz, 1H), 7.32 (dd, J=6.0, 1.0 Hz, 1H), 4.95 (s, 2H), 4.92 (t, J=4.5 Hz, 1H), 4.34 (d, J=5.0 Hz, 2H), 3.61 (s, 3H), 1.37 (s, 9H); MS (ESI+) m/z 496.2 (M+H).

Provenance & Evidence