Hydrochloric Acid → HCID 59380449, compound

Participants

Reaction Steps

A mixture of 7-Bromo-4-chloro[1]benzothieno[2,3-d]pyrimidine (4.85 g, 16.2 mmol), 3-Chloro-4-(pyridin-2-ylmethoxy)-phenylamine (4.73 g, 18.1 mmol, 1.12 equiv), and HCl in dioxane (4.0 M, 7.25 mL) in IPA (100 mL) was heated to reflux for 3 days. The suspension was filtered and washed with IPA (3×20 mL) to collect a light tan solid. The solid was triturated with ether to give a yellow solid. The yellow solid was added to a saturated NaHCO3 solution in a few portions to adjust pH to 7. The suspension was stirred at rt for 5 min then filtered and washed with water and methanol to give a yellow solid. The solid was placed under vacuum oven at 35° C. for 60 h to yield 6.48 g (76%) of product. 1H-NMR (CD3OD) δ 8.81 (d, J=5.4 Hz, 1H), 8.59 (s, 1H), 8.45 (d, J=8.4 Hz, 1H), 8.37 (t, 1H), 8.34 (d, J=2.1 Hz, 1H), 8.04 (d, J=8.2 Hz, 1H), 7.87 (d, J=2.7 Hz, 1H), 7.81 (m, 1H), 7.80 (dd, J=2.1, 8.9 Hz, 1H), 7.63 (dd, J=2.1, 8.9 Hz, 1H), 7.31 (d, J=8.7 Hz, 1H), 5.51 (s, 2H); LCMS RT=3.43 min, [M+H]+=499.0

Provenance & Evidence