Sodium Carbonate → HCID 178483459, compound

Participants

Reaction Conditions

Reaction Steps

In this reaction, the solvents were degased with argon for 10 minutes. A suspension of 7.3 mg PdCl2(dppf), of 29.4 mg (0.24 mmol) of 4-pyridylboronic acid an of 70 mg (0.2 mmol) of trans-(5-Bromo-pyrimidin-2-yl)-[4-(3-dimethylamino-prop-1-ynyl)-cyclohexyl]-methyl-amine in 3.5 ml dioxane were treated with 1 ml of an aqueous solution of 2M Na2CO3. After 17 h at 85° C., 7 mg of PdCl2(dppf) were added and the reaction was heated further at 85° C. for 24 h. The mixture was partitioned between aqueous saturated NaHCO3/Et2O (3×) and the combined organic phases were extracted with 0.1M HCl. The HCl-phase was adjusted to pH 14 (1 N NaOH) and extracted with Et2O (3×). The organic phase was washed with 10% NaCl and dried over Na2SO4 to yield after purifiction with flash-chromatography on silica gel (CH2Cl2/MeOH 99:1 to 9:1) 9 mg (13%) of trans-[4-(3-Dimethylamino-prop-1-ynyl)-cyclohexyl]-methyl-(5-pyridin-4-yl-pyrimidin-2-yl)-amine, MS: 350 (MH+).

Provenance & Evidence