Sodium hydride → HCID 14648837, compound

HRID 1090302Notes

Reaction equation

HRID 1090302 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][CH:12]=[C:11]([OH:15])[C:3]=1[C:4]([O:6][CH2:7][CH2:8][S:9][CH3:10])=[O:5].[H-].[Na+].Cl[C:19]1[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=1>CN(C=O)C>[CH3:28][O:27][C:21]1[CH:22]=[C:23]([O:25][CH3:26])[N:24]=[C:19]([O:1][C:2]2[CH:14]=[CH:13][CH:12]=[C:11]([O:15][C:19]3[N:24]=[C:23]([O:25][CH3:26])[CH:22]=[C:21]([O:27][CH3:28])[N:20]=3)[C:3]=2[C:4]([O:6][CH2:7][CH2:8][S:9][CH3:10])=[O:5])[N:20]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 51523232-Chloro-4,6-dimethoxypyrimidineHCID 14648836HCID 14648836, compound

Product 1

HCID 14648837HCID 14648837, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methylthioethyl 2,6-dihydroxybenzoate (4.5 g) was dissolved in DMF, and 60% sodium hydride (1.6 g) was added thereto. Then, 2-chloro-4,6-dimethoxypyrimidine (3.5 g) was added thereto, and the mixture was heated and reacted at a temperature within a range of from 90 to 110° C. for two hours. The reaction solution was poured into ice water and then extracted twice with ethyl acetate. The ethyl acetate layer was washed with water and dried over anhydrous sodium sulfate. After removing inorganic substances by filtration, the solvent was distilled off under reduced pressure. The residue was purified by column chromatography to obtain the above identified compound as a colorless viscous liquid. (η20D: 1.5706).

Workup

  1. temperaturethe mixture was heated
  2. customreacted at a temperature within a range of from 90 to 110° C. for two hours
  3. extractionextracted twice with ethyl acetate
  4. washThe ethyl acetate layer was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customAfter removing inorganic substances
  7. filtrationby filtration
  8. distillationthe solvent was distilled off under reduced pressure
  9. customThe residue was purified by column chromatography
  10. customto obtain the

Sources & evidence

ORD record
ord-b04e0d7d8e9c4e32809e06cb1a7b66a8
Source dataset
uspto-grants-1992_01
Patent number
US05081244

Reaction notes

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