Morpholine → HCID 68195106, compound

Temperature

200 °C

In a 20 mL vial, 2,4-dichloro-7H-pyrrolo[2,3-d]pyrimidine (0.19 g, 1.011 mmol, 1.0 equiv) was dissolved in NMP (2 mL). Di-isopropyl-ethylamine (0.392 g, 0.514 mL, 3.03 mmol, 3.0 equiv) and morpholine (0.264 g, 0.264 mL, 3.03 mmol, 3.0 equiv.) were then added. The reaction mixture was then transferred into a 5 mL microwave vessel and heated at 200° C. for 30 minutes. The reaction was then cooled down to room temperature and diluted with 35 mL of ethyl acetate. The organic phase was then washed with saturated ammonium chloride solution (2×30 mL). The organic layer was then dried with MgSO4, filtered and removed under reduced pressure to obtain a brown oil. The oil was then purified using flash chromatography using 20% to 100% gradient of EtOAc/Heptane. The compound was isolated as a white solid (239.1 mg, 82% yield). 1HNMR (CDCl3): δ 9.67 (1H, brs), 6.74 (1H, m), 6.29 (1H, d), 3.82 (8H, dt), 3.72 (8H, m)

1. customThe reaction mixture was then transferred into a 5 mL microwave vessel
2. temperatureThe reaction was then cooled down to room temperature
3. washThe organic phase was then washed with saturated ammonium chloride solution (2×30 mL)
4. dry with materialThe organic layer was then dried with MgSO4
5. filtrationfiltered
6. customremoved under reduced pressure
7. customto obtain a brown oil
8. customThe oil was then purified

ORD record

ord-b363b4a7bcd747858d1fdcd25109d84c

Source dataset

uspto-grants-2015_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08987257B2