Dimethylamine → Trifluoroacetic acid

Participants

Reaction Conditions

Reaction Steps

A sealed tube containing 55 mg (0.13 mmol) of 6-chloro-N-(2,6-dichlorophenyl)-1-(3-methoxy-3-methylbutyl)-1H-pyrazolo[3,4-d]pyrimidin-3-amine (prepared as described in Example 1, Step B), 650 μl (2.0 M, 1.3 mmol) of a THF solution of dimethylamine and 120 μl (1.6 mmol) of TFA in 3 mL 1,4-dioxane was heated at 100° C. for 21 h. After this time, 650 μl (2.0 M, 1.3 mmol) of a THF solution of dimethylamine and 120 μl (1.6 mmol) of TFA were added, and heating was continued at 100° C. for an additional 23 h. The orange solution was concentrated, and the residue was purified by HPLC (Capcell Pak C18 5 μm, gradient of 80% A:20% B to 30% A:70% B over 45 min; A=0.5% TFA in water, B=0.5% TFA in acetonitrile) to give the title compound. 1H-NMR (CDCl3) δ 1.25 (s, 6H), 2.01-2.08 (m, 2H), 3.05 (s, 3H), 3.22 (s, 3H), 4.19-4.26 (m, 2H), 6.60 (s, 1H), 7.24 (t, J=8.4 Hz, 1H), 7.46 (d, J=8.1 Hz, 2H), 7.77 (s, 1H), 9.49 (s, 1H). Mass Spectrum (ESI) m/e=409.1.

Provenance & Evidence