Potassium Carbonate → (3S)-N,N-dibenzyl-5-(2-ethylpyrimidin-5-yl)chroman-3-amine

Participants

Reaction Steps

A mixture of (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman -3-amine (278 mg, 0.61 mmol), 5-bromo-2-ethylpyrimidine (114 mg, 0.61 mmol), dichloro[1,1′bis(di-tert-butylphosphino)ferrocene]palladium(II) (24 mg, 0.04 mmol) and 2M potassium carbonate (0.64 mL, 1.28 mmol) in dioxane (6 mL) was irradiated in a microwave under an atmosphere of argon at 140° C. for 1 h. The reaction mixture was filtered through a pad of celite, which was washed with methanol, and the filtrate was concentrated in vacuo. The crude was partioned between ethyl acetate and water and the organic layer was dried and concentrated in vacuo. Purification by column chromatography, using a gradient of ethyl acetate in heptane gave 145 mg (55%) of the desired compound, 1H NMR (400 MHz, DMSO-d6) δ ppm 8.76 (s, 2 H), 7.23-7.35 (m, 8 H), 7.14-7.22 (m, 3 H), 6.78-6.87 (m, 2 H), 4.29-4.39 (m, 1 H), 4.04 (t, 1 H), 3.59-3.75 (m, 4 H), 3.03-3.14 (m, 1 H), 2.92-3.03 (m, 3 H), 2.52-2.57 (m, 1 H, obscured by DMSO), 1.36 (t, 3 H); MS (ESI) m/z 436[M+H+].

Provenance & Evidence