(S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)chroman-3-amine → 5-[(3S)-3-(dibenzylamino)-3,4-dihydro-2H-chromen-5-yl]-N,N-dimethylpyrimidine-2-carboxamide

Participants

Reaction Steps

The title compound was synthesized as described for Intermediate example I-28 in 61% yield starting from (3S)-N,N-dibenzyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan -2-yl)chroman-3-amine and 5-bromo-N,N-dimethylpyrimidine-2-carboxamide. The reaction mixture was irradiated in a microwave at 140° C. for 20 min; 1H NMR (400 MHz, DMSO-d6) δ ppm 8.92 (s, 2 H), 7.23-7.34 (m, 8 H), 7.15-7.22 (m, 3 H), 6.84-6.93 (m, 2 H), 4.31-4.39 (m, 1 H), 4.05 (t, 1 H), 3.60-3.76 (m, 4 H), 3.08-3.15 (m, 1 H), 3.06 (s, 3 H), 2.94-3.05 (m, 1 H), 2.88 (s, 3 H), 2.52-2.59 (m, 1 H); MS (ESI) m/z 452[M+H+].

Provenance & Evidence