Tetrahydrofuran → HCID 54294235, compound

HRID 2293043Notes

Reaction equation

HRID 2293043 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.Cl[S:13]([N:16]=C=O)(=[O:15])=[O:14].I.[CH3:20][N:21]1[C:25](=[O:26])[CH2:24][S:23][C:22]1=N.C([N:30]([CH2:33]C)CC)C.[O:35]1CCCC1>>[CH3:20][N:21]1[C:25](=[O:26])[CH2:24][S:23][CH:22]1[S:13]([N:16]=[N:30][C:33]([NH:1][C:2]1[N:3]=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([O:8][CH3:9])[N:7]=1)=[O:35])(=[O:14])=[O:15]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 21475729HCID 21475729, compound

Product 1

HCID 54294235HCID 54294235, compound

Conditions

Temperature
0 °C

Procedure

1.55 g (10 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 30 ml of dry tetrahydrofuran, and 1.42 g (10 mmol) of chlorosulfonyl isocyanate was dropwise added thereto in a range of from -20° C. to -15° C. The reaction temperature was raised to 0° C., and the mixture was further stirred at the same temperature for 10 minutes. The reaction mixture was cooled again to -30° C., and a mixture comprising 2.84 g (11 mmol) of 3-methyl-2-iminothiazolidin-4-one hydroiodide, 2.22 g (22 mmol) of triethylamine and 30 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 20 minutes. Then, the solvent was distilled off under reduced pressure, and then 100 ml of water was added to the obtained residue. Precipitated crystals were extracted three times with 100 ml of chloroform. The chloroform layer was washed with water and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure. Obtained crystals were washed with a solvent mixture of ethyl ether/acetonitrile and collected by filtration to obtain 1.5 g of desired 1-(3-methylthiazolidin-4-one-2-sulfonylimino)-3-(4,6-dimethoxypyrimidin-2-yl)urea as colorless crystals.

Workup

  1. customof from -20° C. to -15° C
  2. temperatureThe reaction mixture was cooled again to -30° C.
  3. temperatureThe reaction temperature was raised to room temperature
  4. stirringthe mixture was further stirred at the same temperature for 20 minutes
  5. distillationThen, the solvent was distilled off under reduced pressure
  6. addition100 ml of water was added to the obtained residue
  7. customPrecipitated crystals
  8. extractionwere extracted three times with 100 ml of chloroform
  9. washThe chloroform layer was washed with water
  10. dry with materialdried over anhydrous sodium sulfate
  11. distillationThen, the solvent was distilled off under reduced pressure
  12. customObtained crystals
  13. washwere washed with a solvent mixture of ethyl ether/acetonitrile
  14. filtrationcollected by filtration

Sources & evidence

ORD record
ord-69e885ca860b4cfea4b6deeb491ad79d
Source dataset
uspto-grants-1997_11
Patent number
US05686390

Reaction notes

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