Potassium Carbonate → HCID 18936789, compound

HRID 357118Notes

Reaction equation

HRID 357118 reaction equation
[CH2:1]([C:8]1[C:9](=[O:19])[NH:10][C:11](=[O:18])[N:12]2[CH2:17][CH2:16][CH2:15][S:14][C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:27][CH2:28][CH2:29][CH2:30][Cl:31]>CN(C)C=O>[CH2:1]([C:8]1[C:9](=[O:19])[N:10]([CH2:27][CH2:28][CH2:29][CH2:30][Cl:31])[C:11](=[O:18])[N:12]2[CH2:17][CH2:16][CH2:15][S:14][C:13]=12)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 18936848HCID 18936848, compound

Product 1

HCID 18936789HCID 18936789, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 4.11 g (15 mmol) of 9-benzyl-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 70 ml of N,N-dimethylformamide, 3.46 ml (60 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=5/1→2/1) to yield 4.96 g (90.6%, light yellow oily substance) 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=5/1→2/1)

Sources & evidence

ORD record
ord-b1d8eb2ea3ff44fc9dc9c831415ecf9e
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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