N,N-Dimethylaniline → 4-Chloro-1H-pyrazolo[3,4-d]pyrimidine

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Reaction Conditions

Reaction Steps

The 1H-Pyrazolo[3,4-d]pyrimidin-4-ol (5.00 g, 36.73 mmol) was dissolved in 68.5 mL of phosphorous oxychloride and 9.31 mL of N,N-dimethyl aniline (73.47 mmol). This mixture was heated to reflux (120 C) for 90 minutes to completion affording a dark red solution. The mixture was concentrated in vacuo and cooled to 0° C. in an ice bath. The residue was poured into ice water and stirred for three minutes. The acidic melt was extracted with ether, and the organics were combined. The organic was washed with cold water, cold half saturated NaHCO3 solution, brine, separated, dried over MgSO4, filtered, and concentrated in vacuo to afford the 4-chloro-1H-pyrazolo[3,4-d]pyrimidine as a light yellow powder (2.30 g, 41%). 1H NMR (DMSO-d6, 400 MHz) δ 8.84 (s, 1H), 8.46 (s, 1H), NH not observed.

Provenance & Evidence