Azobisisobutyronitrile → tert-Butyl (5-(bromomethyl)pyrazin-2-yl)carbamate

HRID 2199307Notes

Reaction equation

[CH3:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.C1C(=O)N([Br:23])C(=O)C1.CC(N=NC(C#N)(C)C)(C#N)C>C(Cl)(Cl)(Cl)Cl>[Br:23][CH2:1][C:2]1[N:3]=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:14])[CH3:13])=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution tert-butyl 5-methylpyrazin-2-ylcarbamate (500 mg, 2.39 mmol) in CCl4 (8.0 mL) were added NBS(446 mg, 2.51 mmol) and AIBN (117 mg, 0.72 mmol). The reaction mixture was stirred for 4 hours at 80° C. after which, it was partitioned between CH2Cl2 and water. The organic layer was separated and the aqueous layer was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried over MgSO4, celite filtered and concentrated under reduced pressure. The crude product was purified by flash chromatography using (10% Ethyl acetate/Hexane) as a solvent to afford title compound (520 mg, 75% yield). 1H NMR (600 MHz, CDCl3) δ 9.29 (s, 1H), 8.95 (s, 1H), 8.37 (s, 1H), 4.38 (s, 2H), 1.57 (s, 9H). MS m/z: 288 [M+1].

Workup

customwas partitioned between CH2Cl2 and water
customThe organic layer was separated
extractionthe aqueous layer was extracted with CH2Cl2
washThe combined organic extracts were washed with brine
dry with materialdried over MgSO4, celite
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by flash chromatography

Sources & evidence

ORD record: ord-040150ebf74e41118ce4ebf1f490b219
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09358231B2

Reaction notes

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