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0 °C

A solution of 9 mg (0.02 mmol) of N3-(2,6-dimethylphenyl)-1-(2-(oxiran-2-yl)ethyl)-N6-phenyl-1H-pyrazolo[3,4-d]pyrimidine-3,6-diamine 42 (Example 9, Step A) in 2.5 mL of CH2Cl2 was cooled to 0° C. and treated with 120 μl (1.0 M, 0.12 mmol) of a THF solution of LS-Selectride. The resulting tan solution was stirred at 0° C. for 1.25 h. The reaction mixture was quenched with saturated aqueous sodium potassium tartrate (8 mL) and stirred vigorously at room temperature overnight. The mixture was extracted with CH2Cl2 (10 mL), and the organic layer was dried over Na2SO4 and filtered. The filtrate was purified by chromatography on silica gel (eleuens CH2Cl2:MeOH, 98:2) to give the title compound 46. 1H-NMR (CD3OD) δ 1.16 (d, J=6.3 Hz, 3H), 1.80-1.99 (m, 2H), 2.26 (s, 6H), 3.64-3.72 (m, 1H), 4.13-4.23 (m, 2H), 7.00 (t, J=7.4 Hz, 1H), 7.10-7.17 (m, 3H), 7.30 (t, J=8.0 Hz, 2H), 7.75 (d, J=7.7 Hz, 2H), 8.08 (s, 1H). Mass Spectrum (ESI) m/e=403.1 (M+1).

1. customThe reaction mixture was quenched with saturated aqueous sodium potassium tartrate (8 mL)
2. stirringstirred vigorously at room temperature overnight
3. extractionThe mixture was extracted with CH2Cl2 (10 mL)
4. dry with materialthe organic layer was dried over Na2SO4
5. filtrationfiltered
6. customThe filtrate was purified by chromatography on silica gel (eleuens CH2Cl2:MeOH, 98:2)