2-Methyl-3-butyn-2-ol → 2-Methyl-4-{5-[2-(2,2,6,6-tetramethyl-piperidin-4-ylamino)-pyrimidin-4-yl]-thiophen-2-yl}-but-3-yn-2-ol

Participants

Reaction Steps

{4-[5-Bromothiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine, described in Example 5, (300 mg, 0.76 mmol), PdCl2(PPh3)2 (18 mg, 0.025 mmol), 2-methyl-but-3-yn-2-ol (0.3 ml, 2.53 mmol) and CuI (15 mg) were dissolved in triethylamine (25 ml) and refluxed for 1 hour. The reaction mixture was evaporated, taken up in water and extracted 3 times with TBME. The combined organic phases were dried over sodium sulfate, filtered, and purified via chromatography on silicagel (DCM/MeOH/ammonia:95/5/1 to 90/10/1) to give the title compound as white solid, which was crystallized as HCl-salt from EtOH/HCl. Yield: 150 mg (32%).

Provenance & Evidence