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Tetrahydrofuran → 1-(1-Methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea

HRID 2293044
Notes
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Reaction equation

HRID 2293044 reaction equation
[N-:1]=[C:2]=S.[NH2:4][C:5]1[N:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]([O:13][CH3:14])[N:6]=1.Cl[S:16]([N:19]=C=O)(=[O:18])=[O:17].[CH3:22][N:23]1[CH2:27][C:26](=[O:28])[N:25]([CH2:29][CH2:30][CH3:31])[C:24]1=N.C(N(CC)CC)C.[O:40]1CCCC1>>[CH3:22][N:23]1[CH2:27][C:26](=[O:28])[N:25]([CH2:29][CH2:30][CH3:31])[CH:24]1[S:16]([N:19]=[N:1][C:2]([NH:4][C:5]1[N:6]=[C:7]([O:13][CH3:14])[CH:8]=[C:9]([O:11][CH3:12])[N:10]=1)=[O:40])(=[O:17])=[O:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 6

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 542389381-Methyl-3-n-propyl-2-iminoimidazolidin-4-oneHCID 178418790HCID 178418790, compound

Product 1

HCID 53752794
1-(1-Methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea

Conditions

Temperature
0 °C

Procedure

1.16 9 (7.5 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 20 ml of dry tetrahydrofuran, and 1.07 g (7.5 mmol) of chlorosulfonyl isocyanate was dropwise added thereto at -40° C. The reaction temperature was raised to 0° C., and then the reaction mixture was cooled again to -40° C. Then, a mixture comprising 1.16 g (7.5 mmol) of 1-methyl-3-n-propyl-2-iminoimidazolidin-4-one, 0.83 g (8.2 mmol) of triethylamine and 20 ml of dry tetrahydrofuran, was added thereto. The reaction temperature was raised to room temperature, and the mixture was further stirred at the same temperature for 2 hours. Then, the solvent was distilled off under reduced pressure, and then 100 ml of water was added to the obtained residue. The mixture was extracted three times with 100 ml of chloroform. Then, the chloroform layer was washed with water and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and precipitated crystals were washed with a solvent mixture of ethyl ether/acetonitrile and collected by filtration to obtain 0.16 g of desired 1-(1-methyl-3-n-propylimidazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxypyrimidin-2-yl)urea.

Workup

  1. customat -40° C
  2. temperaturethe reaction mixture was cooled again to -40° C
  3. temperatureThe reaction temperature was raised to room temperature
  4. distillationThen, the solvent was distilled off under reduced pressure
  5. addition100 ml of water was added to the obtained residue
  6. extractionThe mixture was extracted three times with 100 ml of chloroform
  7. washThen, the chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent was distilled off under reduced pressure
  10. customprecipitated crystals
  11. washwere washed with a solvent mixture of ethyl ether/acetonitrile
  12. filtrationcollected by filtration

Sources & evidence

ORD record
ord-799ecca7cff14e12b6f6bb643020ac6f
Source dataset
uspto-grants-1997_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05686390

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes