HCID 70345229, compound → HCID 70345394, compound

HRID 1417158Notes

Reaction equation

HRID 1417158 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([C:11]2(O)[C:15]3=[N:16][CH:17]=[CH:18][C:19]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[C:14]3[C:13](=[O:25])[O:12]2)[N:4]=1.B.[Na]>C(O)C>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([CH:11]2[C:15]3=[N:16][CH:17]=[CH:18][C:19]([C:20]4[S:21][CH:22]=[CH:23][CH:24]=4)=[C:14]3[C:13](=[O:25])[O:12]2)[N:6]=1

Participants

4

Reactant 2

HCID 70345229HCID 70345229, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 70345394HCID 70345394, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.7 g of 7-(4,6-dimethoxypyrimidin-2-yl)-7-hydroxy-4-(2-thienyl)furo[3,4-b]pyridin-5(7H)one was dissolved in 30 ml of ethyl alcohol, and while this solution was stirred under cooling with ice, 0.07 g of sodium boron hydride was added thereto. The mixture was stirred at room temperature for 30 minutes, and then the ethyl alcohol was removed by distillation in vacuo. The residue was acidified with 10% hydrochloric acid and extracted with 200 ml of ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/2) to obtain 0.35 g (yield 52.0%) of the desired compound. m.p.: 120°-123° C.

Workup

  1. additionwas added
  2. stirringThe mixture was stirred at room temperature for 30 minutes
  3. customthe ethyl alcohol was removed by distillation in vacuo
  4. extractionextracted with 200 ml of ethyl acetate
  5. washThe extract was washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationThe solvent was distilled off
  8. customthe resulting residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/hexane=1/2)

Sources & evidence

ORD record
ord-70dd159d518b466ab1743bf5deb86e6c
Source dataset
uspto-grants-1999_03
Patent number
US05877120

Reaction notes

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