Hydrochloric Acid → HCID 178423291, compound

Participants

Reaction Conditions

Reaction Steps

The suspension of 4-methoxy-1-(2-methyl-4-piperidylpyrrolo[4,5-d]pyrimidin-6-yl)benzene (Example 71(e)) (0.138 g, 0.43 mmol) in anhydrous CH2Cl2 (12 mL) was cooled to −70° C. under nitrogen atmosphere. Boron tribromide (Aldrich Chemical Company) (0.41 mL, 4.3 mmol) in CH2Cl2 (4 mL) was added dropwise. The reaction mixture was stirred at −70° C. to room temperature for 16 h. The solution was poured into 40 mL of ice-water. The resulting mixture was basified with Et3N to pH 10 and stirred for a period of 3 h. The precipitate that formed was collected by filtration, washed with H2O, and dried in a vacuum oven to give 78.7 mg (60%),of a tan solid. A portion of this material (74 mg, 0.24 mmol) was dissolved in minimum amount of CHCl3 and ethereal hydrogen chloride (1N, 0.26 mL, 0.26 mmol) was added dropwise. The mixture was stirred at room temperature for 20 min. Solvent was then evaporated in vacuo to give a brown solid, which was recrystallized from MeOH/H2O to give 25 mg of the title compound as light-tan crystals. MP:>300° C. (dec). 1H NMR (DMSO-d6; 400 MHz): δ 1.70 (m, 6), 2.55 (s, 3), 4.03 (m, 4), 6.73 (s, 1), 6.93 (d, 2, J=8.54), 7.79 (d, 2, J=8.54), 10.04 (s, 1), 11.75 (br s, 1), 14.15 (br s, 1); MS m/z: 309 (M+1), 307 (M−1). Calcd for C18H21ClN4OH2O: C, 59.58; H, 6.39; N, 15.44. Found: C, 59.13; H, 6.33; N, 15.20.

Provenance & Evidence