Sodium hydride → HCID 11237898, compound

Participants

Reaction Steps

1-(3,5-Bis-trifluoromethyl-phenyl)-4-chloro-1H-pyrazolo[3,4-d]pyrimidine (73 mg, 0.2 mmole), 4-hydroxy-piperidine-1-carboxylic acid tert-butyl ester (0.3 mmole, 1.5 eq) and NaH (1.2 mmol, 6 eq) were dissolved in THF (3 mL) and then stirred at room temperature overnight. THF solvent was removed in vacuo and the oily solid residue was re-dissolved in water and extracted with ethyl acetate provided compound A46 as greenish yellow oil (111 mg, 90%). 1H NMR (CDCl3, 400 MHz) δ 1.48 (s, 9H), 1.88–1.84 (m, 2H), 2.09 (m, 2H), 3.35–3.29 (m, 2H), 3.87–3.80 (m, 2H), 5.62–5.59 (m, 1H), 7.81 (s, 1H), 8.26 (s, 1H), 8.69 (s, 1H), 8.96 (s, 2H). Exact mass calculated for C23H23F6N5O3 531.17, found 532.2 (MH+).

Provenance & Evidence