Potassium Carbonate → HCID 18936797, compound

HRID 357132Notes

Reaction equation

HRID 357132 reaction equation
[S:1]1[CH2:6][CH2:5][CH2:4][N:3]2[C:7](=[O:12])[NH:8][C:9](=[O:11])[CH:10]=[C:2]12.C(=O)([O-])[O-].[K+].[K+].Br[CH2:20][CH2:21][CH2:22][CH2:23][Cl:24]>CN(C)C=O>[Cl:24][CH2:23][CH2:22][CH2:21][CH2:20][N:8]1[C:9](=[O:11])[CH:10]=[C:2]2[S:1][CH2:6][CH2:5][CH2:4][N:3]2[C:7]1=[O:12]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 18936783HCID 18936783, compound

Product 1

HCID 18936797HCID 18936797, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 2.76 g (15 mmol) of 3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione and 3.32 g (24 mmol) of potassium carbonate in 50 ml of N,N-dimethyl-formamide, 3.46 ml (30 mmol) of 1-bromo-4-chlorobutane was added at room temperature, followed by stirring at 60° C. for 2 hours and then at 100° C. for 3 hours. After cooling, the reaction mixture was concentrated to dryness. The residue was dissolved in dichloromethane-water; the organic layer was washed with water and dried. The oily substance obtained by distilling off the solvent was purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1→1/4) to yield 1.92 g (46.6%, white powder) of the desired product.

Workup

  1. additionwas added at room temperature
  2. waitat 100° C. for 3 hours
  3. temperatureAfter cooling
  4. concentrationthe reaction mixture was concentrated to dryness
  5. dissolutionThe residue was dissolved in dichloromethane-water
  6. washthe organic layer was washed with water
  7. customdried
  8. customThe oily substance obtained
  9. distillationby distilling off the solvent
  10. customwas purified by column chromatography (eluent, n-hexane/ethyl acetate=2/1→1/4)

Sources & evidence

ORD record
ord-69d64682424943549a4b88d6121e8bc0
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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