3,4-dihydro-2H-pyran → HCID 14456839, compound

HRID 1649762Notes

Reaction equation

HRID 1649762 reaction equation
[OH:1][CH2:2][CH2:3][S:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[CH:12][N:13]=2)[N:10]=1.[O:14]1[CH:19]=[CH:18][CH2:17][CH2:16][CH2:15]1.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>ClCCCl.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>[O:14]1[CH2:19][CH2:18][CH2:17][CH2:16][CH:15]1[O:1][CH2:2][CH2:3][S:4][C:5]1[CH:6]=[CH:7][C:8]2[N:9]([CH:11]=[CH:12][N:13]=2)[N:10]=1

Participants

6

Reactant 3

HCID 80803,4-dihydro-2H-pyran2×HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 19854391HCID 19854391, compound

Product 1

HCID 14456839HCID 14456839, compoundYield 86.2%

Reagents, catalysts & solvents 2

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)CatalystHCID 111,2-DichloroethaneSolvent

Procedure

In 30 ml of 1,2-dichloroethane is suspended 1.5 g of 6-(2-hydroxyethylthio)imidazo[l,2-b]pyridazine and with stirring at room temperature, 1.94 g of dihydropyran and 193 mg of pyridinium p-toluenesulfonate are added. The mixture is stirred at 65° C. for 4 hours, after which 1.5 g of dihydropyran and 100 mg of pyridinium p-toluenesulfonate are further added. The mixture is stirred for an additional 4 hours. After cooling, the reaction mixture is washed with 30 ml portions of water three times, dried over sodium sulfate, and concentrated under reduced pressure. The residue is subjected to silica gel (100 g) column chromatography and elution is carried out with ethyl acetate. The eluate is concentrated under reduced pressure to give 1.85 g of 6-[2-(2-tetrahydropyranyloxy)ethylthio]imidazo[l,2-b]pyridazine as colorless crystals melting at 60° to 62° C.

Workup

  1. stirringThe mixture is stirred at 65° C. for 4 hours
  2. stirringThe mixture is stirred for an additional 4 hours
  3. temperatureAfter cooling
  4. washthe reaction mixture is washed with 30 ml portions of water three times
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. washThe residue is subjected to silica gel (100 g) column chromatography and elution
  8. concentrationThe eluate is concentrated under reduced pressure

Sources & evidence

ORD record
ord-e556b58e7f0a49d3b9e3a1655bac4b78
Source dataset
uspto-grants-1990_05
Patent number
US04921851

Reaction notes

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