Phenylboronic Acid → 2-Methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine

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Reaction Conditions

Reaction Steps

7-Chloro-2-methylpyrazolo[1,5-a]pyrimidin-5-amine (1J, 10 g, 55 mmol), phenylboronic acid (7.3 g, 60 mmol), and [1,1′-bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (1.0 g, 1.4 mmol) were mixed in dioxane (120 ml) and saturated NaHCO3 (60 ml). The mixture was then heated at 100° C. for 4 hours. After cooling to room temperature, Brine was added and the mixture was extracted with EtOAc five times. Combined organics were washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The crude product was purified by column chromatography (SiO2) to give 2-methyl-7-phenylpyrazolo[1,5-a]pyrimidin-5-amine (10A, 2.2 g, 18%) as a solid. 1H NMR (400 MHz, DMSO-d6) δ=7.95-7.85 (m, 2H), 7.62-7.50 (m, 3H), 6.70 (s, 2H), 6.22 (s, 1H), 5.81 (s, 1H), 2.24 (s, 3H).

Provenance & Evidence