Trimethylsilylacetylene → HCID 68934762, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of of 4-(5-bromo-pyridin-3-yl)-2-(6-methyl-pyridin-2-yl)-7H-pyrrolo[2,3-d]pyrimidine (Example 16) (1 eq, 0.451 mmol, 250 mg) in TEA/DMF (1:1, 6 ml) are added copper (I) iodide (0.1 eq, 0.045 mmol, 8.8 mg), PdCl2(PPh3)2 (0.1 eq, 0.045 mmol, 32.3 mg), and trimethylsilylacetylene (Sigma-Aldrich, St. Louis, USA) (1.5 eq, 0.68 mmol, 0.098 ml). The resulting mixture is stirred at 90° C. for 1 h. The solvents are removed in vacuo, then sat. aqueous NaHCO3 solution is added, and the mixture is extracted with EtOAc. The organic layer is washed with sat. aqueous NaCl solution, dried with MgSO4, and concentrated under reduced pressure. The crude product is purified by reversed phase HPLC and recrystallized in EtOAc giving the title compound; [M+H]+=384.

Provenance & Evidence