Boron tribromide → HCID 86603372, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 34 mg (0.07 mmol) of trans/cis-{6-[4-(2-dimethylamino-ethoxy)-phenyl]-5-phenyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl}-(2-methoxy-cyclobutylmethyl)-amine (Example 35, Step B) in 5 ml dichloromethane was cooled to −78° C. and treated with 80 μl (0.08 mmol) of 1 M solution of BBr3 in dichloromethane. The orange slurry was stirred at −78° C. for 6.5 h, and then was warmed to 0° C. for 20 min. The reaction mixture was quenched with saturated aqueous sodium bicarbonate (5 ml) and stirred overnight. Water was added and the mixture was extracted with dichloromethane (3×). The combined organic layers were dried over Na2SO4, filtered and purified by chromatography on silica gel (CH2Cl2:MeOH, 4:1 grading to CH2Cl2:MeOH, 1:1) to give the title compound. 1H-NMR (CD3OD) δ 0.91-0.99 (m, 1 H), 1.52-1.71 (m, 2 H), 2.03-2.10 (m, 1 H), 2.14-2.24 (m, 1 H), 2.39 (s, 6 H), 2.81 (t, J=4.0 Hz, 2 H), 3.50-3.57 (m, 1 H), 3.61-3.70 (m, 2 H), 4.10 (t, J=4.4 Hz, 2 H), 6.86 (d, J=6.8 Hz, 2 H), 7.27 (d, J=6.8 Hz, 2 H), 7.40 (d, J=6.0 Hz, 2 H), 7.42-7.51 (m, 3 H), 8.16 (s, 1 H). Mass Spectrum (ESI) m/e=458.2 (M+1).

Provenance & Evidence