Sodium Carbonate → HCID 59605657, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vessel was charged with [1-(2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidin-6-ylmethyl)-piperidin-4-yl]-dimethyl-amine (0.400 g, 1.01 mmol), benzo[b]thien-3-ylboronic acid (197 mg, 1.11 mmol), 1 N sodium carbonate solution (2.5 mL), acetonitrile (7.5 mL) and Pd(dppf)Cl2 (82.4 mg. 0.100 mmol), then the mixture was degassed, sealed, and heated at 140° C. under microwave irradiation for 20 min. The reaction mixture was diluted with dichloromethane (100 mL) and 1 N sodium carbonate solution (10 mL) then the phases were separated. The organic phase was washed with saturated aqueous sodium bicarbonate solution (15 mL) then dried (MgSO4) and concentrated in vacuo. Purification by chromatography (silica, 0 to 15% of a 9.5:0.5 MeOH:NH4OH solution in dichloromethane) to afford 146 (240 mg, 48.2%) as a light brown solid. MS m/e 494 [M+H]+ 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 1.47-1.68 (m, 2 H) 1.81 (d, J=12.43 Hz, 2 H) 2.03-2.20 (m, 3 H) 2.28 (s, 6 H) 3.02 (d, J=12.06 Hz, 2 H) 3.80 (s, 2 H) 3.85-3.95 (m, 4 H) 3.99-4.10 (m, 4 H) 7.32 (s, 1 H) 7.34-7.42 (m, 1 H) 7.43-7.53 (m, 1H) 7.89 (d, J=7.91 Hz, 1 H) 8.44 (s, 1 H) 9.00-9.15 (m, 1 H).

Provenance & Evidence