Methanol → 1-(Pyrazin-2-yl)cyclopropane-1-carboxylic acid

A 20% aqueous sodium hydroxide solution (1 mL) was added to a solution of 1-(pyrazin-2-yl)cyclopropanecarbonitrile (0.2 g, 1.37 mmol) in methanol (10 mL) at room temperature. The reaction mixture was heated at reflux for 36 h. The mixture was cooled, and then the solvent was removed under reduced pressure. The resulting residue was partitioned between water and ethyl acetate. The aqueous layer was neutralized with aqueous hydrochloric acid (3N) and the water was removed under reduced pressure. To the residue was added methanol and dichloromethane. The mixture was filtered to remove the insoluble solids and the filtrate was dried over sodium sulfate, filtered and concentrated under reduced pressure to afford the title compound (100 mg). MS (ES−) (M−1) 162.9.

1. temperatureThe reaction mixture was heated
2. temperatureat reflux for 36 h
3. temperatureThe mixture was cooled
4. customthe solvent was removed under reduced pressure
5. customThe resulting residue was partitioned between water and ethyl acetate
6. customthe water was removed under reduced pressure
7. additionTo the residue was added methanol and dichloromethane
8. filtrationThe mixture was filtered
9. customto remove the insoluble solids
10. dry with materialthe filtrate was dried over sodium sulfate
11. filtrationfiltered
12. concentrationconcentrated under reduced pressure

ORD record

ord-23d4c2c1c67a4c6895c9b8c60ba58252

Source dataset

uspto-grants-2016_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09296745B2