Water → HCID 20061258, compound

HRID 1085297Notes

Reaction equation

HRID 1085297 reaction equation
[N:1]1([C:4]2[N:9]([CH3:10])[C:8](=[O:11])[N:7]([CH3:12])[C:6](=[O:13])[C:5]=2[N+:14]([O-:16])=[O:15])[CH2:3][CH2:2]1.[C:17]1([CH3:27])[CH:22]=[CH:21][C:20](S(O)(=O)=O)=[CH:19][CH:18]=1.[OH2:28]>CN(C)C=O>[CH3:10][N:9]1[C:4]([NH:1][CH2:3][CH2:2][N:1]([CH2:4][CH2:5][CH2:27][C:17]2[CH:22]=[CH:21][C:20]([N+:14]([O-:16])=[O:15])=[CH:19][CH:18]=2)[CH2:2][CH2:3][OH:28])=[C:5]([N+:14]([O-:16])=[O:15])[C:6](=[O:13])[N:7]([CH3:12])[C:8]1=[O:11]

Participants

5

Reactant 3

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 20061430HCID 20061430, compound

Product 1

HCID 20061258HCID 20061258, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

An oily substance obtained by dissolving 1.0 g of 6-(aziridin-1-yl)-1,3-dimethyl-5-nitro-2,4(1H,3H)-pyrimidinedione, 0.99 g of N-(2-hydroxethyl)-3-(4-nitrophenyl)propylamine and 50 mg of p-toluenesulfonic acid in 1.0 ml of dimethylformamide was allowed to react at 90° C. for 3 hours. The reaction mixture was cooled down to room temperature, added with 10 ml of water and then vigorously stirred. Crystals formed were collected by filtration, dissolved in chloroform and then subjected to silica gel chromatograph (chloroform/methanol=40:1 (v/v)) for purification. Thus, 0.44 g of 1,3-dimethyl-6-{2-[N-(2-hydroxyethyl)-3-(4-nitrophenyl)propylamino]ethylamino}-5-nitro-2,4(1H,3H)-pyrimidinedione (a free form of compound 180) was obtained.

Workup

  1. customAn oily substance obtained
  2. customto react at 90° C. for 3 hours
  3. customCrystals formed
  4. filtrationwere collected by filtration
  5. dissolutiondissolved in chloroform
  6. customsubjected to silica gel chromatograph (chloroform/methanol=40:1 (v/v)) for purification

Sources & evidence

ORD record
ord-a6f2fa7382f24cf59a64f1045416be67
Source dataset
uspto-grants-1991_04
Patent number
US05008267

Reaction notes

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