Diisopropylamine → HCID 56953202, compound

Participants

Reaction Conditions

Reaction Steps

The mixture of N-(6-chloropyrimidin-4-yl)-2-(2,6-dichlorophenyl)-thiazolo[4,5-d]pyrimidin-7-amine (45 mg, 0.11 mmol), azetidin-3-ol hydrochloride (24 mg, 0.22 mmol) and diisopropylamine (45 mg, 0.35 mmol) in ethanol (1 mL) was heated at 130° C. under microwave radiation for 30 minutes. The reaction mixture was concentrated under reduced pressure. The crude product was purified by reverse phase HPLC (Gemini-NX, 3×10 cm, gradient: 5-85% CH3CN/H2O, 0.1% formic acid/H2O, flow rate 60 mL/min, 10 min) to give the desired compound as a white solid (25 mg, 51% yield). 1H NMR (400 MHz, DMSO-d6) δ 10.94 (s, 1H), 8.85 (s, 1H), 8.31 (d, J=0.8 Hz, 1H), 7.78-7.71 (m, 2H), 7.67 (dd, J=9.4, 6.7 Hz, 1H), 6.54 (s, 1H), 5.79 (d, J=6.5 Hz, 1H), 4.69-4.55 (m, 1H), 4.29-4.18 (m, 2H), 3.76 (dd, J=9.4, 4.4 Hz, 2H). LCMS (Method B): RT=3.55 min, m/z: 446.2 [M+H+].

Provenance & Evidence