Ethyl bromodifluoroacetate → HCID 89619110, compound

Temperature

80 °C

To the Schlank flask containing 2-amino-5-iodopyrimidine (2.210 g, 10.00 mmol) and copper powder (0.953 g, 15.0 mmol) in anhydrous DMSO (10 mL) was added ethyl bromodifluoroacetate (1.285 mL, 10.00 mmol). The reaction mixture was heated at 80° C. under nitrogen overnight. Reaction mixture was cooled to room temperature and diluted with dichloromethane (80 mL) and 2N aqueous ammonium chloride (150 mL). The mixture was extracted with dichloromethane (2×60 mL). The organic layer was washed with brine (2×50 mL), and concentrated. The residue was purified by Biotage SP1 column chromatography on silica gel [40+M], eluting with 5-60% ethyl acetate/hexanes, 24 CV; 60% ethyl acetate/hexanes, 6 column volumes. 1H NMR (500 MHz, DMSO-d6) δ 8.40 (s, 2H), 7.35 (s, 2H), 4.32 (q, J=7.1 Hz, 2H), 1.24 (t, J=7.1 Hz, 3H).

1. customReaction mixture
2. temperaturewas cooled to room temperature
3. extractionThe mixture was extracted with dichloromethane (2×60 mL)
4. washThe organic layer was washed with brine (2×50 mL)
5. concentrationconcentrated
6. customThe residue was purified by Biotage SP1 column chromatography on silica gel [40+M]
7. washeluting with 5-60% ethyl acetate/hexanes, 24 CV

ORD record

ord-bc440ab4a40749c594ceda6353ffd5ba

Source dataset

uspto-grants-2015_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09206199B2