Potassium Carbonate → HCID 56967121, compound

HRID 1507052Notes

Reaction equation

HRID 1507052 reaction equation
Cl[C:2]1[N:7]=[C:6](Cl)[N:5]=[C:4]([NH:9][N:10]2[CH2:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[N:3]=1.[C:17](=[O:20])([O-])[O-].[K+].[K+].[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH2:30])=[CH:27][CH:26]=1>C(#N)C>[CH3:23][O:24][C:25]1[CH:32]=[CH:31][C:28]([CH2:29][NH:30][C:2]2[N:7]=[C:6]([NH:30][CH2:29][C:28]3[CH:31]=[CH:32][C:25]([O:20][CH3:17])=[CH:26][CH:27]=3)[N:5]=[C:4]([NH:9][N:10]3[CH2:14][C:13](=[O:15])[NH:12][C:11]3=[O:16])[N:3]=2)=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 866980651-[(4,6-Dichloro-1,3,5-triazin-2-yl)amino]imidazolidine-2,4-dione

Product 1

HCID 56967121HCID 56967121, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred suspension of 1-(4,6-dichloro-[1,3,5]-triazin-2-yl-amino)-imidazolidine-2,4-dione (770 mg, 2.93 mmol) and potassium carbonate (2.42 g, 17.6 mmol) in acetonitrile (20 mL) at room temperature was added 4-methoxybenzylamine (0.96 mL, 7.32 mmol). The reaction mixture was stirred for 24 h at room temperature under an atmosphere of nitrogen and then the solvent was removed under reduced pressure. The residue was extracted with ethyl acetate and the ethyl acetate was dried (MgSO4) and evaporated to give the crude product which was purified by flash chromatography on silica using CH2Cl2/MeOH (50:1→10:1) as eluent. The pure product was isolated as a colourless solid (587 mg, 43%). 1H NMR (d6 DMSO): δ=3.67 (s, 6H); 3.96 and 4.05 (2 s, total 214); 4.20 and 4.32 (2 s, total 4H); 6.80 (bs, 4H); 7.13-7.39 (m, 6H); 8.67, 8.85 and 8.99 (2 s, total 1H); 11.0 (bs, 1H). Mass spectrum (ES+) 465 (M+H).

Workup

  1. customthe solvent was removed under reduced pressure
  2. extractionThe residue was extracted with ethyl acetate
  3. dry with materialthe ethyl acetate was dried (MgSO4)
  4. customevaporated
  5. customto give the crude product which
  6. customwas purified by flash chromatography on silica

Sources & evidence

ORD record
ord-e1a9462171484291b182d70452e70d25
Source dataset
uspto-grants-2015_12
Patent number
US09221799B2

Reaction notes

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