Water → HCID 71611704, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methyl-N2-((1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)pyrimidine-2,4-diamine (108 mg, 0.22 mmol) and tetrabutyl ammonium fluoride (580 mg, 2.2 mmol) in tetrahydrofuran (20 mL) was heated at 80° C. for 18 h. The reaction mixture was poured into water (100 mL) and the pH was adjusted to ca. 10 by adding an NH4OH solution. The mixture was extracted with EtOAc (50 mL×3) and the combined extracts dried (MgSO4), filtered, and concentrated under reduced pressure. The residue was purified by reverse phase preparative HPLC to afford 18 mg (22.7%) of N2-((1H-pyrrolo[2,3-c]pyridin-4-yl)methyl)-N4-(5-cyclopropyl-1H-pyrazol-3-yl)-N2-methylpyrimidine-2,4-diamine as a white solid. 1H NMR (500 MHZ, MeOD-d4) δ 8.62 (s, 1H), 7.82 (d, 2H), 7.59 (d, 1H), 6.59 (d, 1H), 6.12 (d, 1H), 5.84 (brs, 1H), 5.13 (s, 2H), 3.03 (s, 3H), 1.58 (brs, 1H), 0.68 (d, 2H), 0.27 (d, 2H); MS (ESI): m/z=361.2 [M+1]+.

Provenance & Evidence