Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1) → HCID 59272339, compound

HRID 1970267Notes

Reaction equation

HRID 1970267 reaction equation
[CH3:1][C:2]([CH3:28])([CH3:27])[CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12](=O)[C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[N:22][CH:23]=[N:24][CH:25]=4)[CH:16]=[CH:17][C:18]=3[O:19][C:10]=2[CH:9]=[CH:8][N:7]=1.[CH3:29][Mg]Br.C1(C)C=CC(S([O-])(=O)=O)=CC=1.[NH+]1C=CC=CC=1>C1COCC1.C(Cl)(Cl)Cl.C(Cl)Cl>[CH3:28][C:2]([CH3:1])([CH3:27])[CH2:3][CH2:4][O:5][C:6]1[C:11]2[C:12](=[CH2:29])[C:13]3[CH:14]=[C:15]([C:20]4[CH:21]=[N:22][CH:23]=[N:24][CH:25]=4)[CH:16]=[CH:17][C:18]=3[O:19][C:10]=2[CH:9]=[CH:8][N:7]=1

Participants

7

Reactant 3

HCID 466102Benzenesulfonic acid, 4-methyl-, compd. with pyridine (1:1)HCID 592723821-(3,3-dimethylbutoxy)-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-oneHCID 178418573HCID 178418573, compound

Product 1

HCID 59272339HCID 59272339, compound

Reagents, catalysts & solvents 3

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 1-(3,3-dimethylbutoxy)-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridin-10-one (0.320 g, 0.852 mmol) in THF (8.00 mL) was cooled to 0° C. and methylmagnesium bromide (3.0 M in diethyl ether) (0.483 mL, 1.449 mmol) was added dropwise. The mixture stirred at 0° C. for 1 h. The mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution and diluted with EtOAc. The aqueous phase was separated and extracted with EtOAc. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford a yellow film. This material was dissolved in chloroform (8.00 mL), pyridinium p-toluenesulfonate (10.71 mg, 0.043 mmol) was added, and the mixture was heated at reflux for 2 h. The reaction mixture was diluted with DCM and the solution was partitioned between DCM and saturated aqueous sodium bicarbonate solution. The aqueous phase was separated and extracted with DCM. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to afford 1-(3,3-dimethylbutoxy)-10-methylene-8-(pyrimidin-5-yl)-10H-chromeno[3,2-c]pyridine as a yellow solid. MS m/z=374.2 [M+H]+. Calcd for C23H23N3O2: 373.4.

Workup

  1. customThe mixture was quenched at 0° C. with saturated aqueous ammonium chloride solution
  2. additiondiluted with EtOAc
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto afford a yellow film
  10. temperaturethe mixture was heated
  11. temperatureat reflux for 2 h
  12. customthe solution was partitioned between DCM and saturated aqueous sodium bicarbonate solution
  13. customThe aqueous phase was separated
  14. extractionextracted with DCM
  15. washThe combined organic phases were washed with brine
  16. dry with materialdried over anhydrous sodium sulfate
  17. filtrationfiltered
  18. concentrationconcentrated

Sources & evidence

ORD record
ord-95f3b6b90e654d789898819618167528
Source dataset
uspto-grants-2013_04
Patent number
US08426447B2

Reaction notes

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