1-Phenylethanol → 5-chloro-N-(1-methyl-1H-pyrazol-4-yl)-4-(1-phenylethoxy)-7H-pyrrolo[2,3-d]pyrimidin-2-amine

Participants

Reaction Steps

To a solution of 2,4,5-trichloro-7H-pyrrolo[2,3-d]pyrimidine (3.00 g, 13.4 mmol) in 1,4-dioxane (45 mL) was added potassium t-pentoxide (31.2 mL, 1.7 M in toluene) followed by 1-phenylethanol (1.62 mL, 13.4 mmol). The reaction solution was stirred at ambient temperature for 0.5 hr. To the same reaction vessel, 1-methyl-1H-pyrazol-4-amine (1.96 g, 20.2 mmol) and BrettPhos Palladacycle (214 mg, 0.020 mmol) were added and nitrogen gas was bubbled through the reaction mixture for 5 min. The reaction mixture was then sealed and heated to 80° C. for 2 hrs. A black precipitate was filtered off and washed with EtOAc. The combined filtrates were combined and diluted with water (75 mL), extracted EtOAc (2×75 mL), washed with brine, dried over sodium sulfate, filtered and concentrated under in vacuo. The crude residue was purified by flash chromatography (eluting with a gradient of 30%-100% EtOAc in heptanes) to give the title compound (1.76 g, 34%) as a green foam. m/z (APCI+) for C18H17ClN6O 369.1/370.2 (M+H)+.

Provenance & Evidence