{4-[5-(3-Amino-3-methyl-but-1-ynyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine → {4-[5-((E)-3-Amino-3-methyl-but-1-enyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine

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Reaction Steps

A solution of {4-[5-(3-Amino-3-methyl-but-1-ynyl)-thiophen-2-yl]-pyrimidin-2-yl}-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine (Example 5, 100 mg, 0.252 mmol) in 10 ml of THF and LAH (1M in THF, 0.25 ml, 0.25 mmol) was refluxed for 3 hours, poured on 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:90/10/1 to 85/15/2) to give the title compound as yellow solid. Yield: 20 mg (20%).

Provenance & Evidence