Cesium carbonate → HCID 86679636, compound

Participants

Reaction Conditions

Reaction Steps

To a microwave reaction vial was added 2-chloro-4-(3-nitrophenoxy)-5-(pyridin-3-yl)-7-{[2-(trimethylsilyl)ethoxy]methyl}-7H-pyrrolo[2,3-d]pyrimidine (130 mg, 0.26 mmol), 1-methyl-1H-pyrazol-4-amine (28 mg, 0.29 mmol, 1.1 mol eq), 1,4-dioxane (5 mL), Cs2CO3 (ca. 170 mg), Xantphos (16 mg) and Pd2(dba)3 (24 mg). The reaction vial was flushed with nitrogen, capped, stirred and heated to 140° C. using microwave at high absorption level for 45 min. The reaction was diluted with EtOAc (120 mL) and water (20 mL). The organic layer was separated, washed with water (20 mL) and with brine (10 mL), dried over Na2SO4 and evaporated to give crude product (TLC: Rf 0.2 in 100 ethyl acetate). The crude product was purified on silica to give the title compound as a green gum (290 mg, 100% yield). 1H NMR (400 MHz, methanol-d4) δ ppm 8.99 (s, 1H) 8.48 (d, J=3.78 Hz, 1H) 8.18-8.32 (m, 3H) 7.71-7.81 (m, 2H) 7.48-7.55 (m, 2H) 5.70 (s, 2H) 3.77-3.87 (m, 2H) 3.70-3.77 (m, 3H) 0.94-1.06 (m, 2H) 0.00 (s, 9H). m/z (APCI+) for C27H30N8O4Si 559.1 (M+H)+.

Provenance & Evidence