Potassium Carbonate → 5-[4-(4-Methyl-benzylamino)-6-(4-methoxybenzylamino)-[1,3,5]-triazin-2-ylamino]-3-methyl-imidazolidine-2,4-dione

HRID 76338Notes

Reaction equation

HRID 76338 reaction equation
Cl[C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=2)[N:5]=[C:4]([NH:17][CH:18]2[NH:22][C:21](=[O:23])[N:20]([CH3:24])[C:19]2=[O:25])[N:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:32][O:33][C:34]1[CH:41]=[CH:40][C:37]([CH2:38][NH2:39])=[CH:36][CH:35]=1>CN(C)C=O.O>[CH3:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:6]2[N:7]=[C:2]([NH:39][CH2:38][C:37]3[CH:40]=[CH:41][C:34]([O:33][CH3:32])=[CH:35][CH:36]=3)[N:3]=[C:4]([NH:17][CH:18]3[NH:22][C:21](=[O:23])[N:20]([CH3:24])[C:19]3=[O:25])[N:5]=2)=[CH:11][CH:12]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 754524-MethoxybenzylamineHCID 866980665-[4-Chloro-6-(4-methyl-benzylamino)-[1,3,5]-triazin-2-ylamino]-3-methyl-imidazolidine-2,4-dione

Product 1

HCID 569672345-[4-(4-Methyl-benzylamino)-6-(4-methoxybenzylamino)-[1,3,5]-triazin-2-ylamino]-3-methyl-imidazolidine-2,4-dioneYield 77.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred suspension of 5-[4-chloro-6-(4-methyl-benzylamino)-[1,3,5]-triazin-2-ylamino]-3-methyl-imidazolidine-2,4-dione (Example 1.5, Part A) (80 mg, 0.22 mmol) and potassium carbonate (67 mg, 0.49 mmol) in dimethylformamide (5 mL) at 35° was added 4-methoxybenzylamine (0.03 mL, 0.24 mmol). The reaction mixture was stirred at 35° for 20 h and then diluted with water and extracted with ethyl acetate. The ethyl acetate layer was dried and concentrated to give the crude product as a foam (79 mg, 77%). NMR spectrum δH (300 MHz, CD3CN): 7.2-7.0 (br m, 7H, Ar+NH), 6.8 (br d, 2H, Ar), 6.5 (br, 1H, NH), 6.1-5.8 (br m, 2H, NH), 5.45 (br d, 1H, CH), 4.5-4.3 (br, 4H, CH2), 4.15 (d, 2H, CH2) 3.74 (s, 3H, OMe), 2.9-2.7 (br, 3H, NMe), 2.3 (s, 3H, Me). Mass spectrum (ESI) m/z 463 [M+H].

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe ethyl acetate layer was dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-53f785bb999f4fc380abfb65408b17aa
Source dataset
uspto-grants-2014_09
Patent number
US08835629B2

Reaction notes

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