Sodium hydride → HCID 56953203, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of cyclopropylcarboxamide (19 mg, 0.22 mmol) in DMF (1.5 mL) at 0° C. was added NaH (9.8 mg, 0.24 mmol). The reaction mixture was stirred at 0° C. for 10 minutes. A solution of 2-(2,6-dichlorophenyl)-7-(methylsulfonyl)thiazolo[4,5-d]pyrimidine (940 mg, 0.11 mmol) in DMF (0.5 mL) was then added at 0° C. The reaction mixture was warmed to room temperature and stirred for 2 hours. The reaction was quenched with ice-water and extracted with EtOAc (3×25 mL). The combined organic extract was dried over Na2SO4 and concentrated under reduced pressure. The crude product was purified by reverse phase HPLC (Gemini-NX, 3×10 cm, gradient: 30-70% CH3CN/H2O, 0.1% NH4OH/H2O, flow rate 60 mL/min, 10 min) to give the desired compound as a yellow solid (12 mg, 31%). 1H NMR (400 MHz, DMSO-d6) δ 11.89 (s, 1H), 8.98 (s, 1H), 7.75-7.70 (m, 2H), 7.66 (dd, J=9.4, 6.6 Hz, 1H), 2.19-2.10 (m, 1H), 0.95 (tt, J=7.6, 4.2 Hz, 4H). LCMS (Method B): RT=4.69 min, m/z: 365.0 [M+H+].

Provenance & Evidence