HCID 10090741, compound → HCID 19011976, compound

HRID 1729299Notes

Reaction equation

HRID 1729299 reaction equation
[NH2:1][C:2]1[CH:27]=[CH:26][C:5]([O:6][CH2:7][CH2:8][CH2:9][N:10]2[CH2:15][CH2:14][N:13]([C:16]3[N:21]([CH3:22])[C:20](=[O:23])[N:19]([CH3:24])[C:18](=[O:25])[CH:17]=3)[CH2:12][CH2:11]2)=[CH:4][CH:3]=1>O1CCCC1.ClCCl.CN=C=O>[CH3:22][N:21]1[C:16]([N:13]2[CH2:12][CH2:11][N:10]([CH2:9][CH2:8][CH2:7][O:6][C:5]3[CH:26]=[CH:27][C:2]([NH:1][C:18]([NH:19][CH3:20])=[O:25])=[CH:3][CH:4]=3)[CH2:15][CH2:14]2)=[CH:17][C:18](=[O:25])[N:19]([CH3:24])[C:20]1=[O:23]

Participants

4

Reactant 1

HCID 10090741HCID 10090741, compound

Product 1

HCID 19011976HCID 19011976, compoundYield 179.3%

Reagents, catalysts & solvents 2

HCID 12228Methyl IsocyanateSolventHCID 21919333Tetrahydrofurane dichloromethaneSolvent

Procedure

1.5 g of 6-[4-(3-[4-aminophenoxy]propyl)piperazin-1-yl]-1,3-dimethyl-2,4(1H,3H)-pyrimidinedione obtained in Example 6 was dissolved in a mixed solvent of tetrahydorfuran/dichloromethane (15 ml/10 ml), and 0.26 ml of methyl isocyanate was added to the solution at room temperature, followed by stirring for 20 hours. The precipitated crystals were collected by filtration, and then washed with a small amount of cooled dichloromethane, thereby obtaining 1.55 g (yield: 90%) of 1,3-dimethyl-6-[4-(3-[4-(N'-methylureido)phenoxy]propyl)piperazin-1-yl]-2,4(1H,3H)-pyrimidinedione.

Workup

  1. additionwas added to the solution at room temperature
  2. filtrationThe precipitated crystals were collected by filtration
  3. washwashed with a small amount of cooled dichloromethane

Sources & evidence

ORD record
ord-2917d97577224c00ac8d29ee2c6bd34b
Source dataset
uspto-grants-1994_07
Patent number
US05332739

Reaction notes

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