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

HRID 709298Notes

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-fbcfee93f2a146bd9faeb9b3cf919dd8
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09180127B2

Reaction notes

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