1,4-Benzodioxan-6-ylamine → N-(2,3-Dihydro-1,4-benzodioxin-6-yl)-4-[2-(3-nitrophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-[2-(methylsulfinyl)-4-pyrimidinyl]-2-(3-nitrophenyl)pyrazolo[1,5-a]pyridine (1.32 g, 3.49 mmol) in ethanol (4.0 mL) is added 1,4-benzodioxan-6-amine (0.56 mL, 4.54 mmol) and conc. HCl (3 drops). The dark mixture is heated in a microwave apparatus at 160° C. for 20 min. The mixture is monitored, and heated for an additional 10 min. The mixture is diluted with DCM and concentrated to a brown foam. The crude material is purified by silica gel chromatography (30-50% EtOAc/hexanes) to give the desired product (1.09 g). 1H NMR (400 MHz, d6-DMSO) δ 9.36 (s, 1H), 8.88 (d, 1H, J=6.8), 8.45 (s, 1H), 8.28-8.31 (m, 3H), 8.01-8.03 (m, 1H), 7.72 (t, 1H, J=8.0), 7.47-7.51 (m, 1H), 7.13-7.18 (m, 2H), 6.97-6.95 (m, 1H), 6.63-6.65 (m, 2H), 4.14 (m, 1H), 7.13-7.18 (m, 2H), 6.95-6.97 (m, 1H), 6.63-6.65 (m, 2H), 4.14 (s, 4H).

Provenance & Evidence