Water → (Pyrimidin-4-yl)acetonitrile

To a suspension of LiH (404 mg, 50.79 mmol) in anhydrous THF (10 mL), was added dropwise a solution of 2-pyridylacetonitrile (3 g, 25.39 mmol) in anhydrous THF (10 mL). The reaction mixture was stirred at zero degree for 1 hour. A solution of 2,4-dichloro-5-methyl-pyrimidine (4.55 g, 27.93 mmol), dissolved in anhydrous THF (5 ml), was added dropwise at zero degree. The reaction mixture was stirred and heated to reflux for 14 hours. The reaction mixture was allowed to warm to r.t. and water was added (20 mL). THF was evaporated under vacuum and a solution of 1N HCl (20 mL) was added. The precipitate was filtered and washed with water (10 mL) and cyclohexanes (10 mL) to give a yellow solid which was dried under vacuum at 40 degrees. The yellow crystalline product 4-pyrimidineacetonitrile, 2-chloro-5-methyl-alpha-2(1H)-pyridinylidene was isolated. (5.5 g, 90%).

1. additionwas added dropwise at zero degree
2. stirringThe reaction mixture was stirred
3. temperatureheated
4. temperatureto reflux for 14 hours
5. customTHF was evaporated under vacuum
6. additiona solution of 1N HCl (20 mL) was added
7. filtrationThe precipitate was filtered
8. washwashed with water (10 mL) and cyclohexanes (10 mL)
9. customto give a yellow solid which
10. customwas dried under vacuum at 40 degrees

ORD record

ord-4b676fe3b95442a08e414806132675c0

Source dataset

uspto-grants-2010_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07855212B2