N-bromobutanimide → HCID 118863786, compound

HRID 60357Notes

Reaction equation

HRID 60357 reaction equation
[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][CH:20]=3)[CH:16]=[CH:17][C:11]=2[N:10]([CH3:26])[C:9]1=[O:27])(=[O:3])[CH3:2].C1C(=O)N([Br:35])C(=O)C1>C(Cl)Cl.O>[C:1]([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:18][C:19]3[CH:20]=[CH:21][C:22]([Cl:25])=[CH:23][CH:24]=3)[CH:16]=[C:17]([Br:35])[C:11]=2[N:10]([CH3:26])[C:9]1=[O:27])(=[O:3])[CH3:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 118863777HCID 118863777, compound

Product 1

HCID 118863786HCID 118863786, compoundYield 66.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H, 4H,5H)-yl)propyl acetate (1.50 g, 3.85 mmol) in DCM (1 mL) was added NBS (0.68 g, 3.85 mmol). The reaction was stirred at RT for 1 h then diluted with DCM (10 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by chromatography eluted with PE/EA (5:1 to 1:1) to give 3-(7-bromo-5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (1.2 g, 66.5% yield) as a solid. LCMS: MH+ 468 and TR=1.777 min. Used without further purification.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated to a residue which
  3. customwas purified by chromatography
  4. washeluted with PE/EA (5:1 to 1:1)

Sources & evidence

ORD record
ord-de464cb2fb0c453b9bb2958affa16ffd
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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