N-bromobutanimide → HCID 86702427, compound

HRID 2278437Notes

Reaction equation

[CH3:1][CH:2]1[O:7][CH:6]([CH3:8])[CH2:5][N:4]([C:9]2[N:14]=[C:13]([C:15]3[CH:19]=[CH:18][O:17][C:16]=3[CH3:20])[CH:12]=[CH:11][N:10]=2)[CH2:3]1.[Br:21]N1C(=O)CCC1=O>C(Cl)(Cl)Cl.O>[Br:21][C:12]1[C:13]([C:15]2[CH:19]=[CH:18][O:17][C:16]=2[CH3:20])=[N:14][C:9]([N:4]2[CH2:3][C@H:2]([CH3:1])[O:7][C@H:6]([CH3:8])[CH2:5]2)=[N:10][CH:11]=1

Participants

Conditions

Temperature: 0 °C

Procedure

2,6-Dimethyl-4-[4-(2-methyl-3-furanyl)-2-pyrimidinyl]morpholine (737 mg, 2.70 mmol) was dissolved in chloroform (13 mL), cooled in an ice bath and treated with N-bromosuccinimide (480 mg, 2.70 mmol). The resulting mixture was stirred at 0° C. for 1 hour. The reaction mixture was diluted with water and extracted with ethyl acetate (×2). The ethyl acetate layers were combined, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by SP4 Biotage column chromatography eluting with a gradient of 0-20% ethyl acetate in iso-hexane. Product containing fractions were combined and evaporated under reduced pressure to give the title compound (719 mg, 2.041 mmol, 76% yield) as a white solid. LC/MS [M+H]+=352/354.

Workup

temperaturecooled in an ice bath
extractionextracted with ethyl acetate (×2)
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customThe residue was purified by SP4 Biotage column chromatography
washeluting with a gradient of 0-20% ethyl acetate in iso-hexane
additionProduct containing fractions
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-36552d5e016b499b8f53d1f5a2909d27
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133178B2

Reaction notes

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