Sodium borohydride → 3-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propan-1-ol

Participants

Reaction Steps

A slurry of 27 mg (0.07 mmol) of crude 3-(3-(2,6-dimethylphenylamino)-6-(phenylamino)-1H-pyrazolo[3,4-d]pyrimidin-1-yl)propanal 36 (Example 4, Step A) in 4 mL of absolute ethanol was treated with 17 mg (0.4 mmol) of NaBH4. The resulting orange slurry was stirred at room temperature for 2 h. The reaction mixture was quenched with water (10 mL) and concentrated. The residue was extracted with CH2Cl2 (3×20 mL). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (eluens CH2Cl2:MeOH, 96:4) to give the title compound 37. 1H-NMR (CD3OD) δ1.96-2.04 (m, 2H), 2.26 (s, 6H), 3.54 (t, J=6.3 Hz, 2H), 4.20 (t, J=6.7 Hz, 2H), 6.99 (dt, J=7.4 Hz, 0.9 Hz, 1H), 7.09-7.17 (m, 3H), 7.30 (t, J=7.6 Hz, 2H), 7.75 (dd, J=8.6 Hz, 0.9 Hz, 2H), 8.09 (s, 1H). Mass Spectrum (ESI) m/e=389.2 (M+1).

Provenance & Evidence