Cyclobutylamine → HCID 136500837, compound

Participants

Reaction Conditions

Reaction Steps

A glass microwave reaction vessel was charged with 6-(3-fluoro-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (Example 264; 60 mg, 0.203 mmol) and cyclobutylamine (0.173 mL, 2.032 mmol) in DMSO (0.6 mL). The reaction was heated in an oil bath at 50° C. for 15 min. The mixture was purified by rpHPLC (Phenomenex Gemini C18 column (100×50 mm, 10 μm), 90 mL/min, 5-40% ACN in water with 0.1% TFA). Product-containing fractions were combined and ACN was removed in vacuo. The residual mixture was neutralized with saturated aq. NaHCO3, and the suspension was filtered and dried to give 6-(3-(cyclobutylamino)-2-methylquinoxalin-5-yl)-3H-pyrrolo[2,3-d]pyrimidin-4(7H)-one (15 mg, 0.043 mmol, 21% yield) as a yellow solid. MS (ESI, pos. ion) m/z: 347.1 (M+1); 1H NMR (400 MHz, DMSO-d6) δ ppm 12.69 (brs, 1H), 11.97 (brs, 1H), 8.10 (1H, d, J=7.2 Hz), 7.90 (1H, br. s.), 7.66 (1H, d, J=7.0 Hz), 7.47 (1H, br. s.), 7.37 (2H, br. s.), 4.50 (1H, br. s.), 2.58 (3H, br. s.), 2.16-2.28 (2H, m), 1.83-1.97 (2H, m).

Provenance & Evidence