Tetrahydrofuran → HCID 53857969, compound

HRID 1451203Notes

Reaction equation

HRID 1451203 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].[CH2:19]([N:22]1[CH:27]=[CH:26][CH2:25][S:24][C:23]1=N)[CH2:20][CH3:21].C([N:31]([CH2:34]C)CC)C.[O:36]1CCCC1>>[CH2:19]([N:22]1[CH:27]=[CH:26][CH2:25][S:24][CH:23]1[S:13]([N:16]=[N:31][C:34]([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:36])(=[O:14])=[O:15])[CH2:20][CH3:21]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 70918Chlorosulfonyl isocyanateHCID 1189462-Amino-4,6-dimethoxypyrimidineHCID 54169012HCID 54169012, compound

Product 1

HCID 53857969HCID 53857969, compound

Conditions

Temperature
-40 °C

Procedure

0.32 g (2.06 mmol) of 2-amino-4,6-dimethoxypyrimidine was dissolved in 40 ml of dry tetrahydrofuran, and the solution was cooled to -40° C. At the same temperature, 0.29 g (2.05 mmol) of chlorosulfonyl isocyanate was dropwise added thereto. Then, the temperature was raised to 0° C. The mixture was cooled again to -40° C., and then a mixed solution comprising 0.4 g (2.56 mmol) of 3,6-dihydro-3-n-propyl-2H-1,3-thiazin-2-imine, 0.26 g (2.57 mmol) of triethylamine and 40 ml of dry tetrahydrofuran, was dropwise added thereto. The mixture was gradually heated to room temperature with stirring, and then the solvent was distilled off under reduced pressure. 100 ml of water was added to the residue, and then the mixture was extracted twice with 50 ml of chloroform. The chloroform layer was washed with water and then dried over anhydrous sodium sulfate. Then, chloroform was distilled off under reduced pressure. Obtained crystals were washed with acetonitrile and then with ethyl ether to obtain 0.3 g of desired 1-(3,6-dihydro-3-n-propyl-2H-1,3-thiazine-2-sulfonylimino)-3-(4,6-dimethoxyprimidin-2-yl)urea. Melting point: 161°-163° C.

Workup

  1. temperatureThen, the temperature was raised to 0° C
  2. temperatureThe mixture was cooled again to -40° C.
  3. temperatureThe mixture was gradually heated to room temperature
  4. distillationthe solvent was distilled off under reduced pressure
  5. addition100 ml of water was added to the residue
  6. extractionthe mixture was extracted twice with 50 ml of chloroform
  7. washThe chloroform layer was washed with water
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThen, chloroform was distilled off under reduced pressure
  10. customObtained crystals
  11. washwere washed with acetonitrile

Sources & evidence

ORD record
ord-7e2a8efc92ec44ef8c9973bb27c43b02
Source dataset
uspto-grants-1997_02
Patent number
US05604179

Reaction notes

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