HCID 70346079, compound → HCID 70345538, compound

HRID 1417160Notes

Reaction equation

HRID 1417160 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[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:14]3[C:13](=[O:26])[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[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=4)=[C:14]3[C:13](=[O:26])[O:12]2)[N:6]=1

Participants

4

Reactant 2

HCID 70346079HCID 70346079, compoundHCID 178418435HCID 178418435, compound

Product 1

HCID 70345538HCID 70345538, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1 g of 7-(4,6-dimethoxypyrimidin-2-yl)-7-hydroxy-4-phenylfuro[3,4-b]pyridin-5(7H)one was dissolved in 30 ml of ethanol, and 0.1 g of sodium boron hydride was added thereto at room temperature. The mixture was stirred at room temperature for 6 hours, and the ethanol was distilled off. Ice water was added to the residue, and the mixture was adjusted to pH 2-3 with dilute hydrochloric acid and then extracted with ethyl acetate. The extract was sufficiently washed with water and dried over anhydrous magnesium sulfate, and then the solvent was distilled off. The resulting crude product was purified by silica gel column chromatography to obtain 0.7 g (yield 73%) of the desired compound. m.p.: 151°-153.5° C.

Workup

  1. customat room temperature
  2. distillationthe ethanol was distilled off
  3. additionIce water was added to the residue
  4. extractionextracted with ethyl acetate
  5. washThe extract was sufficiently washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off
  8. customThe resulting crude product was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-6308693686d8440a8e661da16155a9ae
Source dataset
uspto-grants-1999_03
Patent number
US05877120

Reaction notes

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