Acetone → HCID 11519283, compound

Participants

Reaction Steps

A solution of 26 mg (0.1 mmol) of N-allyl-4-{5-phenyl-4-[(tetrahydro-furan-2-ylmethyl)-amino]-7H-pyrrolo[2,3-d]pyrimidin-6-yl}-benzenesulfonamide (Example 12) in 2.8 ml acetone and 1 ml water was treated with 62 μl (0.005 mmol) of a 2.5 wt. % solution of OsO4 in tert-butanol and 19 mg (0.2 mmol) of 4-methylmorpholine-N-oxide. The yellow solution was stirred at room temperature for 26 h, then was quenched with water (10 ml) and extracted with dichloromethane (3×). The combined organic layers were dried over Na2SO4, filtered, and the filtrate was purified by chromatography on silica gel (CH2Cl2:MeOH, 22:3) to give the title compound. 1H-NMR (DMSO-d6) δ 1.29-1.40 (m, 1 H), 1.53-1.84 (m, 3 H), 2.40-2.49 (m, 1 H), 2.53-2.63 (m, 1 H), 2.82-2.90 (m, 1 H), 3.21-3.59 (m, 6 H), 3.69-3.77 (m, 1 H), 4.51 (t, J=5.6 Hz, 1 H), 4.75 (d, J=5.1 Hz, 1 H), 4.97-5.03 (m, 1 H), 7.37-7.42 (m, 3 H), 7.44-7.53 (m, 5 H), 7.65 (d, J=8.5 Hz, 2 H), 8.21 (s, 1 H), 12.34 (br s, 1 H). Mass Spectrum (ESI) m/e=524.0 (M+1).

Provenance & Evidence