Aluminium lithium hydride → [1-(2-aminopyrimidin-4-yl)-6-bromo-1H-indazol-3-yl]methanol

Participants

Reaction Steps

To a solution ethyl 1-(2-aminopyrimidin-4-yl)-6-bromo-1H-indazole-3-carboxylate (500 mg, 0.88 mmol) in dry THF (4 mL) at 0° C. under an atmosphere of nitrogen was introduced lithium aluminium hydride (3.5 mL of a 1M solution in THF, 3.50 mmol). After 10 minutes at this temperature, the reaction mixture was quenched by carefully transferring into a rapidly stirred saturated aqueous solution of Rochelle's salt (5 mL). The suspension was extracted with DCM (10 mL) and the organic extract filtered through a pad of Celite®. The filtrate was washed with water (5 mL) and brine (5 mL), dried (Na2SO4), filtered and the filtrate concentrated in vacuo to furnish the crude title compound as a colorless solid: 1H NMR (250 MHz, DMSO) delta 4.84 (2H, d, J=5.48 Hz), 5.61 (1H, t, J=5.71 Hz), 7.04 (3H, s), 7.51 (1H, dd, J=8.45, 1.75 Hz), 7.92 (1H, d, J=8.53 Hz), 8.28 (1H, d, J=5.48 Hz), 9.11 (1H, d, J=1.22 Hz); LC-MS: m/z=+319.90/321.80 (M+H)+. This compound, with LC-MS purity=76% UV, was used in the next step without further purification.

Provenance & Evidence