Diisopropylethylamine → N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-7-{2-[(diethylamino)methyl]acryloyl}-5,6,7,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidin-4-amine

Participants

Reaction Steps

To a suspension of [3-Chloro-4-(pyridin-2-ylmethoxy)-phenyl]-(5,6,7,8-tetrahydro-9-thia-1,3,7-triaza-fluoren-4-yl)amine (0.053 g, 0.00034 mol), 2-Diethylaminomethyl-acrylic acid (0.12 g, 0.00028 mol), O-(Benzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium tetrafluoroborate (0.109 g, 0.00033 mol) in mixture of dichloromethane/tetrahydrofuran (1.2/1.2 ml) was added diisopropylethylamine (0.148 ml, 0.001 mol) slowly over 15 min. The mixture was stirred at room temperature for 16-18 hours. Reaction was judged complete by TLC (Eluent: 10% MeOH/DCM). The reaction mixture was concentrated to dryness under vacuum, dissolved in MeOH (1.5 ml), filtered and subjected to reverse phase HPLC purification to give the desired product (0.0173 g, 11.0%) of the desired product. 1H-NMR (CD2Cl2) δ 8.60 (d, 1H), 8.45 (s, 1H), 7.80 (m, 2H), 7.63 (d, 1H), 7.41 (m, 1H), 7.28 (m, 1H), 7.04 (m, 2H), 5.38 (d, 2H), 5.25 (s, 2H), 4.85 (s, 2H), 4.05 (m, 2H), 3.20 (m, 4H), 2.52 (br, d, 4H), 0.98 (br, d, 6H); LCMS RT=2.32 min; [M+H]+=563.1.

Provenance & Evidence