Binap, (A+-)- → HCID 58015857, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-Chloro-5-methyl-7-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidine (15 mg, 0.06 mmol), 4-(6-Amino-pyridin-3-yl)-piperazine-1-carboxylic acid tert-butyl ester (20.5 mg, 0.075 mmol), Pd2(dba)3 (2.8 mg, 0.0031 mmol), BINAP (3.82 mg, 0.0061 mmol), sodium tert-butoxide (8.84 mg, 0.092 mmol), and 1,4-dioxane (4 mL) under nitrogen is heated in a sealed tube apparatus at 100° C. for 2.5 h. After cooling to room temperature the reaction mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried (anhydrous Na2SO4) and the solvent is evaporated. The crude product is dissolved in DCM (2 mL) and TFA (0.5 ml was added). The solution is stirred at room temperature. The reaction mixture is diluted with ethyl acetate and washed with brine. The organic phase is dried (anhydrous Na2SO4) and the solvent is evaporated. The crude product is purified by hplc to afford (5-Methyl-7-pyridin-2-yl-7H-pyrrolo[2,3-d]pyrimidin-2-yl)-(5-piperazin-1-yl-pyridin-2-yl)-amine as a pale yellow solid (27%, two steps). 1H NMR (400 MHz, DMSO-d6) 8.80-8.81 (m, 2H), 8.51 (s, 1H), 8.12 (d, J=5.0 Hz, 1H), 8.0-8.11 (m, 1H), 8.0 (d, J=2.9 Hz, 1H), 7.90 (s, 1H), 7.49 (d, J=2.4 Hz, 1H), 7.32 (d, J=2.4 Hz, 1H), 3.04-3.06 (m, 4H), (2.86-2.89 (m, 4H), 2.32 (s, 3H). MS (ESI) m/z 387.09 [M+H]+.

Provenance & Evidence