Potassium Carbonate → HCID 56967121, compound

HRID 76332Notes

Reaction equation

HRID 76332 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 (2s, total 2H); 4.20 and 4.32 (2s, total 4H); 6.80 (bs, 4H); 7.13-7.39 (m, 6H); 8.67, 8.85 and 8.99 (2s, 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-cea42191067a4d068d6e9a3c25112e94
Source dataset
uspto-grants-2014_09
Patent number
US08835629B2

Reaction notes

Loading…