Sodium Hydroxide → (2,3-Dihydro-benzo[1,4]dioxin-6-ylmethyl)-{2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethyl}-amine

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A solution of 2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethylamine (77 mg, 286 μmol), 2,3-dihydro-benzo[1,4]dioxine-6-carbaldehyde (47 mg, 286 μmol) and p-toluenesulfonic acid monohydrate (5 mg, 26 μmol) in dioxane (3 mL) was heated at 60° C. for 16 h. Sodium triacetoxyborohydride (180 mg, 860 μmol) was then added. The reaction mixture was stirred at r.t. for 1 h. EtOAc (25 mL) and 1N NaOH (25 mL) were then added. The organic layer was isolated, dried (MgSO4), filtered, and concentrated. Silica gel chromatography (0% to 10% MeOH/DCM) afforded 69 mg (57%) of (2,3-dihydro-benzo[1,4]dioxin-6-ylmethyl)-{2-[2-(2-imidazol-1-yl-6-methyl-pyrimidin-4-yl)-pyrrolidin-1-yl]-ethyl}-amine. [M+H]+ 421.23; 1H NMR (400 MHz, CDCl3) δ 8.60 (s, 1H), 7.89 (s, 1H), 7.23 (s, 1H), 7.12 (s, 1H), 6.68-6.79 (m, 3H), 4.21 (s, 4H), 3.54 (t, 1H), 3.22 (m, 1H), 2.70-2.82 (m, 2H), 2.20-2.60 (m, 9H), 1.84 (m, 2H), 1.70 (m, 1H).

Provenance & Evidence