Potassium Carbonate → HCID 10292512, compound

Participants

Reaction Conditions

Reaction Steps

A solution of Example 1F (41 mg) in degassed DME (1.3 mL) was treated with 5-(4,4,5,5-tetramethyl-(1,3,2)dioxaborolan-2-yl)-pyrimidin-2-ylamine (41.5mg, prepared according to the procedure described in Tetrahedron Letters, 1997, 38, 3447-3450), tetrakis(triphenylphosphine)palladium (12 mg) and a degassed 2 N solution of potassium carbonate in water (0.2 mL). The tube was sealed, heated to 70° C., and stirred for 20 hours. The reaction mixture was then cooled to room temperature, concentrated, and diluted with dichloromethane (4 mL). The precipitate was removed by filtration and washed with water (10 mL) and then cold acetone (3 mL) to provide the desired product. MS (ESI(+)) m/e 370 (M+H)+; 1H NMR (300 MHz, MeOH) δ 8.49 (s, 2H), 7.61 (dd, J=2.1, 12 Hz, 1H), 7.57 (t, J=8.4 Hz, 1H), 7.32 (dd, J=2.1, 8.7 Hz, 1H), 4.8 (m, 1H), 4.16 (t, J=9 Hz, 1H), 3.83 (dd, J=6.3, 9.6 Hz, 1H), 3.56(d, J=5.4 Hz, 2H), 1.96 (s, 3H).

Provenance & Evidence