Potassium Carbonate → HCID 18936642, compound

HRID 357125Notes

Reaction equation

HRID 357125 reaction equation
[CH:1]([C:4]1[C:5](=[O:15])[NH:6][C:7](=[O:14])[N:8]2[CH2:13][CH2:12][CH2:11][S:10][C:9]=12)([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:23][CH2:24][CH2:25][CH2:26][Cl:27]>CN(C)C=O>[Cl:27][CH2:26][CH2:25][CH2:24][CH2:23][N:6]1[C:5](=[O:15])[C:4]([CH:1]([CH3:3])[CH3:2])=[C:9]2[S:10][CH2:11][CH2:12][CH2:13][N:8]2[C:7]1=[O:14]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 813641-Bromo-4-chlorobutaneHCID 18936859HCID 18936859, compound

Product 1

HCID 18936642HCID 18936642, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To a suspension of 1.81 g (8 mmol) of 9-isopropyl-3,4-dihydro-2H,6H-pyrimido[6,1-b][1,3]thiazine-6,8(7H)-dione and 1.77 g (12.8 mmol) of potassium carbonate in 30 ml of N,N-dimethylformamide, 1.84 ml (16 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 2.12 g (83.6%, colorless oily substance) of the desired product. 1H-NMR (CDCl3, 200 MHz) δ 1.28 (6H, d, J=6.8 Hz), 1.77-1.86 (4H, m), 2.15-2.26 (2H, m), 3.08 (2H, t, J=6.8 Hz), 3.13 (1H, quint., J=7.0 Hz), 3.41-3.60 (2H, m), 3.95 (2H, t, J=7.2 Hz), 4.04-4.10 (2H, m); IR (neat) 2956, 1691, 1637, 1560, 1439, 777, 752 cm-1

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-0176e55a085e4c82b792c52f8eebc848
Source dataset
uspto-grants-1998_11
Patent number
US05840732

Reaction notes

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