Phenol → HCID 11584042, compound

Participants

Reaction Conditions

Reaction Steps

To a vial containing [4-chloro-2-(2,6-diethyl-phenyl)-6-methyl-pyrimidin-5-ylmethyl]-methyl-(1S)-(1,2,3,4-tetrahydro-naphthalen-1-yl)-amine 9 (0.1 mL of a 0.2 M DMA solution, 0.02 mmol) is added phenol (0.1 mL of a 0.3 M DMA solution, 0.03 mmol) and KOtBu (0.1 mL of a 0.3 M solution in 7:3 DMA:tBuOH, 0.03 mmol) and allowed to stir at 70° C. for 16 h. EtOAc (50 mL) and sat. NaHCO3 (50 mL) are then added and the organic layer is washed with water (100 mL), brine (100 mL) and dried over Na2SO4. The crude solution is filtered, concentrated and purified by SiO2 flash chromatography using hexanes:Et2O (5:1) affording (1S)-N-{[2-(2,6-diethylphenyl)-4-methyl-6-phenoxypyrimidin-5-yl]methyl}-N-methyl-1,2,3,4-tetrahydronaphthalen-1-amine as a colorless oil. [mass expected (491.67); mass found (491.42)].

Provenance & Evidence