Sodium hydride → HCID 57496307, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-hydroxy-piperidine-1-carboxylic acid isopropyl ester (727 mg, 3.88 mmol), and sodium hydride (465 mg, 19.4 mmol) in THF (12 mL) was stirred for 30 min at 60° C. 1-(4-Bromo-phenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine was added to the mixture at room temperature and stirred for 1.0 hr at RT. The reaction was quenched with water and the product extracted in ethyl acetate. The organic layer was concentrated in vacuo to provide Compound A220 as a white solid (1.3 g, 81%). 1H NMR (CDCl3, 400 MHz) δ 1.19 (d, 6H), 1.73–1.85 (m, 2H), 1.98–2.08 (m, 2H), 3.26–3.34 (m, 2H), 3.78–3.87 (m, 2H), 4.88 (h, 1H), 5.54 (h, 1H), 7.57 (d, 2H), 8.07 (d, 2H), 8.13 (s, 1H), 8.55 (s, 1H). Exact mass calculated for C20H22BrN5O3 460.3, found 462.3 (MH+).

Provenance & Evidence