1,3-Dibromo-5,5-dimethylhydantoin → 1-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)ethanone

HRID 1099262Notes

Reaction equation

HRID 1099262 reaction equation
[NH2:1][C:2]1[C:7]2=[CH:8][CH:9]=[C:10]([C:11](=[O:13])[CH3:12])[N:6]2[N:5]=[CH:4][N:3]=1.[Br:14]N1C(C)(C)C(=O)N(Br)C1=O>CN(C=O)C>[NH2:1][C:2]1[C:7]2=[C:8]([Br:14])[CH:9]=[C:10]([C:11](=[O:13])[CH3:12])[N:6]2[N:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 592321291-{4-Aminopyrrolo[2,1-f][1,2,4]triazin-7-yl}ethan-1-one

Product 1

HCID 592320001-(4-Amino-5-bromopyrrolo[2,1-f][1,2,4]triazin-7-yl)ethanoneYield 190.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 1-(4-aminopyrrolo[2,1-f][1,2,4]triazin-7-yl)ethanone (262.0 mg, 1.49 mmol) in DMF (21 mL) was added 1,3-dibromo-5,5-dimethylhydantoin (212.6 mg, 0.74 mmol). The mixture was stirred for 80 min and then quenched by addition of saturated aqueous sodium sulphite (10 mL) and water (60 mL). The mixture was allowed to warm to rt and the precipitate was collected by filtration. The solid was air-dried to yield 360.0 mg (95%) of the title compound. 1H-NMR (DMSO-d6) δ 9.49 (bs, 1H), 8.49 (bs, 1H), 8.12 (s, 1H), 7.64 (s, 1H), 2.56 (s, 3H); MS [M+H]+=255.3; LCMS RT=1.96 min.

Workup

  1. customquenched by addition of saturated aqueous sodium sulphite (10 mL) and water (60 mL)
  2. filtrationthe precipitate was collected by filtration
  3. customThe solid was air-dried

Sources & evidence

ORD record
ord-d3730331f1b64af3905fa7d97fc9a38d
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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