Potassium Carbonate → 1-[4-Chloro-6-(4-methoxybenzyl)amino-{1,3,5}-triazin-2-yl-amino]-imidazolidine-2,4-dione

HRID 76340Notes

Reaction equation

HRID 76340 reaction equation
Cl[C:2]1[N:7]=[C:6]([Cl:8])[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([O-])([O-])=O.[K+].[K+].[CH3:23][O:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][NH2:32])=[CH:27][CH:26]=1>CC#N>[Cl:8][C:6]1[N:7]=[C:2]([NH:32][CH2:31][C:28]2[CH:29]=[CH:30][C:25]([O:24][CH3:23])=[CH:26][CH:27]=2)[N:3]=[C:4]([NH:9][N:10]2[CH2:14][C:13](=[O:15])[NH:12][C:11]2=[O:16])[N:5]=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 866980691-[4-Chloro-6-(4-methoxybenzyl)amino-{1,3,5}-triazin-2-yl-amino]-imidazolidine-2,4-dioneYield 66%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of 1-(4,6-dichloro-[1,3,5]-triazin-2-yl-amino)-imidazolidine-2,4-dione (Example 1.1, Part A) (3.84 g, 14.6 mmol) and K2CO3 (4.4 g, 31.8 mmol) in CH3CN (50 mL) was added (4-methoxyphenyl)-methanamine (2.0 g, 14.6 mmol) drop-wise at 0° C. The mixture was stirred at r.t. overnight. TLC showed the reaction was complete. The mixture was filtered and the cake was portioned between water and EtOAc. The organic layer was separated, and the aqueous layer was extracted with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated in vacuo to give the expected compound (3.50 g, yield: 66%) as a white solid. It was used for the next step without further purification. δH (400 MHz, DMSO-d6): 11.30-11.23 (m, 1H), 10.06-9.83 (m, 1H), 8.67-8.60 (m, 1H), 7.24-7.13 (m, 2H), 6.90-6.83 (m, 2H), 4.40-4.35 (m, 2H), 4.26-4.05 (m, 2H), 3.73 (s, 3H). Mass spectrum (ESI) m/z 364 (100%, MH+).

Workup

  1. filtrationThe mixture was filtered
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1eac722e09f5458a85089d0914b7739c
Source dataset
uspto-grants-2014_09
Patent number
US08835629B2

Reaction notes

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