Triethylamine → HCID 178423288, Verbindung

To a −78° C. solution of 1-[2,7-dimethyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl]-3-methoxybenzene (Example 139) (0.89 g, 2.76 mmol) in CH2Cl2 (40 mL) under a N2 atmosphere was added 1 M BBr3 (5.50 mL, 5.50 mmol). The reaction mixture was allowed to warm to room temperature. The mixture was stirred at room temperature for an additional 20 h. The reaction mixture was then poured onto ice-water (200 mL) and the pH of the aqueous solution was adjusted to pH 9 with the addition of NEt3 (2 mL). CH2Cl2 (60 mL) added and the resulting mixture was stirred at room temperature for 2 h. The mixture was transferred to a separatory funnel. The organic solution was separated, washed with H2O (100 mL), saturated NaCl (100 mL), dried (MgSO4), filtered and concentrated under reduced pressure to afford 0.90 g (100%) of 3-[2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl]phenol as a beige colored solid. This compound (0.90 mg, 5.00 mmol) was dissolved in 5:1:1 EtOAc/MeOH/CH2Cl2 (40 mL) and heated to boiling. To the hot solution was added 1 M ethereal HCl (5.00 mL, 5.00 mmol). The solution was allowed to cool to room temperature. The resulting solid was collected by filtration, washed with EtOAc (2×10 mL), Et2O (3×5 mL) and dried under vacuum at 60° C. to give 525 mg (55%) of the title compound as white colored crystals. Mp: >280° C. 1H HMR (DMSO-d6; 400 MHz): δ 1.63 (br s, 6), 2.48 (s, 3), 3.97 (br s, 4), 6.73 (s, 1), 6.84-6.87 (m, 1), 7.24 (br s, 1), 7.27-7.28 (m, 2), 9.75 (s, 1), 11.61 (s, 1), 13.87 (s, 1). MS m/z: 309 (M+1 for free base). Anal. Calcd for C18H20N4O.HCl.1.3H2O: C, 58.70; H, 6.46; N, 15.22; Cl, 9.63. Found: C, 59.09; H, 6.11; N, 14.91; Cl, 9.30.