3-Methylmorpholine → 5-(3-Methylmorpholino)-2-morpholinopyridin-3-amine

Temperature

65 °C

To a stirred solution of 5-bromo-2-morpholinopyridin-3-amine (0.5 g, 1.94 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (0.074 g, 0.16 mmol), Pd2dba3 (0.071 g, 0.08 mmol) and 3-methylmorpholine (0.98 g, 9.7 mmol) in THF (3.9 mL). To this mixture was added LHMDS in THF (1.0 M, 10.65 mL, 10.65 mmol) and the resulting reaction was heated to 65° C. The reaction was stirred for 2.25 h. After which, the reaction was cooled to rt and then poured into water (50 mL) and extracted with EtOAc (2×50 mL) and DCM (2×50 mL). The combined organic layers were dried over magnesium sulfate and the crude product was purified on basic alumina (0-100% EtOAc/hexane) to give 5-(3-methylmorpholino)-2-morpholinopyridin-3-amine. Mass Spectrum (ESI) m/e=279.2 (M+1).

1. customthe resulting reaction
2. temperatureAfter which, the reaction was cooled to rt
3. extractionextracted with EtOAc (2×50 mL) and DCM (2×50 mL)
4. dry with materialThe combined organic layers were dried over magnesium sulfate
5. customthe crude product was purified on basic alumina (0-100% EtOAc/hexane)

ORD record

ord-19230917c8d04d4d98110c960c62ec92

Source dataset

uspto-grants-2015_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08940724B2