Sodium hydride → HCID 10480339, compound

Participants

Reaction Steps

To a solution of 1-tert-butylazetidin-3-ol (24 mg, 0.19 mmol) and 7-chloro-3-(4-chlorophenyl)-2-(2-chlorophenyl)-5-methylpyrazolo[1,5-a]pyrimidine (I-3A-4b; 36 mg, 0.093 mmol) in THF (1 ml) was added NaH (60% dispersion in oil, 9.3 mg, 0.23 mmol). After stirring for 1 hour, the reaction was quenched with water, extracted from saturated aqueous NaHCO3 with ethyl acetate, the combined organic layers were dried (MgSO4), concentrated and purified on a Biotage™ Flash 12M column using 0–5% methanol in methylene chloride as eluant to afford 9A-1 (26 mg, 59%) as a colorless solid: +ESI MS (M+1) 481.4; 1H NMR (400 MHz, CD2Cl2) δ 7.50–7.36 (m, 6H), 7.24 (d, J=8.7 Hz, 2H), 5.99 (s, 1H), 5.10–5.02 (m, 1H), 3.76–3.70 (br m, 2H), 3.49–3.43 (br m, 2H), 2.60 (s, 3H), 1.00 (s, 9H).

Provenance & Evidence