Tetrahydrofuran → HCID 54083436, compound

HRID 1451204Notes

Reaction equation

HRID 1451204 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.N=[C:21]1[N:25]([CH3:26])[CH2:24][CH2:23][O:22]1.C([N:29]([CH2:32]C)CC)C.[O:34]1CCCC1>>[CH3:26][N:25]1[CH2:24][CH2:23][O:22][CH:21]1[S:13]([N:16]=[N:29][C:32]([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:34])(=[O:14])=[O:15]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 21475756HCID 21475756, compound

Product 1

HCID 54083436HCID 54083436, compound

Conditions

Temperature
-5 °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 at -20° C. The reaction temperature was raised to -5° C., and the mixture was stirred at the same temperature for 5 minutes. The reaction mixture was cooled again to -20° C., and a mixture comprising 2.28 g (10 mmol) of 2-imino-3-methyloxazolidine 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 one hour. Then, the solvent was distilled off under reduced pressure, and then 100 ml of water was added to the obtained residue. Precipitated crystals were collected by filtration, washed with water and then with a solvent mixture of ethyl ether/acetonitrile and dried to obtain 0.8 g of desired 1-(3-methloxazolidine-2-sulfonylimino)-3-(4,6-dimethoxypyrimidin-2-yl)urea. Melting point: 174°-175° C.

Workup

  1. customat -20° C
  2. temperatureThe reaction mixture was cooled again to -20° C.
  3. temperatureThe reaction temperature was raised to room temperature
  4. stirringthe mixture was further stirred at the same temperature for one hour
  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. filtrationwere collected by filtration
  9. washwashed with water
  10. additionwith a solvent mixture of ethyl ether/acetonitrile
  11. customdried

Sources & evidence

ORD record
ord-082d9b4d968c471e917f0ece749980f4
Source dataset
uspto-grants-1997_02
Patent number
US05604179

Reaction notes

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