p-Toluenesulfonic acid → HCID 59361778, compound

Participants

Reaction Steps

5-(3—CHloro-4-(3-fluorobenzyloxy)phenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (prepared according to a similar procedure as described in Example 1) (1 equivalent) is placed in THF. Triphenyl phosphine (1.5 equivalents) is added, followed by dropwise addition of DEAD (3 equivalents). 3-(1,3-dioxolan-2-yl)cyclohexanol (1 equivalent) is added and the mixture is stirred at room temperature overnight. The reaction mixture is partitioned between EtOAc and water, the organic layer is separated, washed with water, brine, dried over Na2SO4 and filtered. The filtrate is concentrated under reduced pressure and suspended in acetone. p-Toluensulfonic acid (0.6 equivalent) is added and the mixture is refluxed for 4 h. The mixture is filtered, the filtrate is concentrated in vacuo and purified by column chromatography.

Provenance & Evidence