1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

HRID 1099251Notes

Reaction equation

HRID 1099251 reaction equation
[N:1]1([CH2:7][C:8]2[N:16]3[C:11]([C:12]([NH2:17])=[N:13][CH:14]=[N:15]3)=[CH:10][CH:9]=2)[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Br:18]N1C(C)(C)C(=O)N(Br)C1=O>C1COCC1>[Br:18][C:10]1[CH:9]=[C:8]([CH2:7][N:1]2[CH2:6][CH2:5][O:4][CH2:3][CH2:2]2)[N:16]2[C:11]=1[C:12]([NH2:17])=[N:13][CH:14]=[N:15]2

Participants

4

Reactant 2

HCID 64791,3-Dibromo-5,5-dimethylhydantoinHCID 592319487-(Morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine

Product 1

HCID 592320545-Bromo-7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amineYield 160.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-(morpholin-4-ylmethyl)pyrrolo[2,1-f][1,2,4]triazin-4-amine (562 mg, 2.40 mmol) in THF (19 ml) at −20 C was added 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione (344 mg, 1.2 mmol) in three portions. The reaction was stirred at −20 C for 3 h. Upon the completion, the reaction was quenched with aqueous saturated Na2SO3 and allowed to warm up to rt. The crude was extracted with ethyl acetate. The organic was washed with brine, dried over Na2SO4 and concentrated. The resulting crude was purified via column chromatography (95:5 v/v CH2Cl2—CH3OH) to afford 600 mg of the title compound as yellow solid (yield 79%). 1H-NMR (DMSO-d6) δ 7.84 (s, 1H), 6.71 (s, 1H), 3.74 (s, 2H), 3.51 (t, J=4 Hz, 4H), 2.37(t, J=4 Hz, 4H); MS [M+H]+=312; LCMS RT=1.04 min.

Workup

  1. customUpon the completion, the reaction was quenched with aqueous saturated Na2SO3
  2. extractionThe crude was extracted with ethyl acetate
  3. washThe organic was washed with brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customThe resulting crude was purified via column chromatography (95:5 v/v CH2Cl2—CH3OH)

Sources & evidence

ORD record
ord-a6822ec60ff04fb18fb29695196af696
Source dataset
uspto-grants-2012_03
Patent number
US08143393B2

Reaction notes

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