N-bromobutanimide → [2-Bromo-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester

HRID 408910Notes

Reaction equation

HRID 408910 reaction equation
[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]2[CH2:19][NH:18][C:17](=[O:20])[NH:16][CH2:15]2)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:29])C(=O)C1>CC#N>[C:1]([O:5][C:6](=[O:21])[NH:7][C:8]1[CH:9]=[CH:10][C:11]([CH:14]2[CH2:19][NH:18][C:17](=[O:20])[NH:16][CH2:15]2)=[CH:12][C:13]=1[Br:29])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 59771203[4-(2-Oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester

Product 1

HCID 59771302[2-Bromo-4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl esterYield 32%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of [4-(2-oxo-hexahydro-pyrimidin-5-yl)-phenyl]-carbamic acid tert-butyl ester (as prepared in the previous step, 29 mg, 0.10 mmol) in CH3CN (1 mL), NBS (19.5 mg, 0.100 mmol) was added. The resulting mixture was stirred overnight and concentrated to half the volume. The resulting precipitate was collected by filtration to obtain the title compound (12 mg, 32%): Mass spectrum (ESI, m/z): Calcd. for C15H20BrN3O3, 370.0 and 372.0 (M+H). found 370.1 and 372.1.

Workup

  1. concentrationconcentrated to half the volume
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-bf44d13225854476beb83a8da9bfa473
Source dataset
uspto-grants-2014_06
Patent number
US08759347B2

Reaction notes

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