Pyridine → Phenyl 5-cyanopyrazin-2-ylcarbamate

HRID 1019727Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=1.C(Cl)Cl.N1C=CC=CC=1.[C:19]1([O:25][C:26](Cl)=[O:27])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C1COCC1.O>[C:19]1([O:25][C:26](=[O:27])[NH:1][C:2]2[CH:7]=[N:6][C:5]([C:8]#[N:9])=[CH:4][N:3]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

Conditions

Temperature: 50 °C

Procedure

2-Amino 5-cyano pyrazine (0.25 g, 2.08 mmol) was dissolved in THF and DCM (3:1, 40 mL) and pyridine (0.49 g, 6.2 mmol) was added. The mixture was stirred for 15 minutes. Phenylchloroformate (0.97 g, 6.2 mmol) was added and the reaction mixture was heated at 50° C. for 2 hours. The reaction mixture was cooled to RT and DCM (40 mL) and water (25 mL) were added. The separated organic layer was washed with water (2×25 mL), brine (25 mL), dried (Na2SO4) and the solvents evaporated under reduced pressure. The product was purified by column chromatography on neutral silica gel using 15-20% EtOAc in hexane to give the title compound (0.29 g, 54%).

Workup

temperatureThe reaction mixture was cooled to RT
washThe separated organic layer was washed with water (2×25 mL), brine (25 mL)
dry with materialdried (Na2SO4)
customthe solvents evaporated under reduced pressure
customThe product was purified by column chromatography on neutral silica gel using 15-20% EtOAc in hexane

Sources & evidence

ORD record: ord-46c75e57b2934b078495f621f7e7c926
Source dataset: uspto-grants-2014_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08716287B2

Reaction notes

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