Tetrahydrofuran → HCID 67253094, compound

Participants

Reaction Conditions

Reaction Steps

A solution of [6-(2-chloro-pyrimidin-4-yloxy)-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl]-acetic acid ethyl ester (0.50 g, 1.38 mmol) in THF (10 mL) was treated with 2,4-dimethoxybenzylamine (0.41 mL, 2.73 mmol) followed by triethylamine (0.77 mL, 5.52 mmol). The mixture was heated at 60° C. in a sealed tube for 2 days. The solid was filtered and the filtrate was concentrated in vacuo. The residue was purified by preparative HPLC (CH3CN/0.1% formic acid in water) to give {6-[2-(2,5-dimethoxy-benzylamino)-pyrimidin-4-yloxy]-1-hydroxy-4-methyl-1,3-dihydro-benzo[c][1,2]oxaborol-3-yl}-acetic acid ethyl ester as a light yellow solid (0.35 g, 51%). 1H NMR (400 MHz, CD3OD) δ 8.04 (d, J=5.71 Hz, 1H), 7.17 (s, 1H), 7.04 (s, 1H), 6.60-6.22 (m, 3H), 6.14 (d, J=5.71 Hz, 1H), 5.69-5.64 (m, 1H), 4.10-4.00 (m, 4H), 3.78 (s, 3H), 3.75 (s, 3H), 3.16 (dd, J=14.91, 2.86 Hz, 1H), 2.43 (dd, J=14.91, 8.73 Hz, 1H), 2.36 (s, 3H), 1.20 (t, J=7.30 Hz, 3H).

Provenance & Evidence