Triethylamine → (1R,5S)-3-(5-bromo-4-methylpyrimidin-2-yl)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid

Temperature

75 °C

In a 40 mL vial were mixed 5-bromo-2-chloro-4-methylpyrimidine (438 mg, 2.109 mmol), (1R,5S)-3-azabicyclo[3.1.0]hexane-2-carboxylic acid (295 mg, 2.320 mmol), and Et3N (0.882 mL, 6.33 mmol) in EtOH (90 mL). The resulting yellow solution was stirred at 75° C. for 3 days. The reaction mixture was subsequently partitioned between 1N HCl (40 mL) and EtOAc (40 mL). The phases were separated and the aqueous layer was back-extracted with EtOAc (75 mL). The organic layers were combined, washed with brine (40 mL), dried over Na2SO4, filtered, and concentrated to give the title compound as a white solid, which was used without further purification (660 mg).

1. customThe reaction mixture was subsequently partitioned between 1N HCl (40 mL) and EtOAc (40 mL)
2. customThe phases were separated
3. extractionthe aqueous layer was back-extracted with EtOAc (75 mL)
4. washwashed with brine (40 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated

ORD record

ord-f036e74a37cf4e0286b15f3995a815a7

Source dataset

uspto-grants-2016_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09434743B2