Tetrahydrofuran → HCID 70346543, compound

HRID 1417156Notes

Reaction equation

HRID 1417156 reaction equation
C([C:3]1([C:18]2[N:23]=[C:22]([O:24][CH3:25])[CH:21]=[C:20]([O:26][CH3:27])[N:19]=2)[C:7]2=[N:8][CH:9]=[CH:10][C:11]([C:12]3[O:13][CH:14]=[CH:15][CH:16]=3)=[C:6]2[C:5](=[O:17])[O:4]1)#N.[O:28]1CCCC1.[OH-].[Na+]>O>[CH3:25][O:24][C:22]1[CH:21]=[C:20]([O:26][CH3:27])[N:19]=[C:18]([C:3]2([OH:28])[C:7]3=[N:8][CH:9]=[CH:10][C:11]([C:12]4[O:13][CH:14]=[CH:15][CH:16]=4)=[C:6]3[C:5](=[O:17])[O:4]2)[N:23]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 70346645HCID 70346645, compound

Product 1

HCID 70346543HCID 70346543, compoundYield 94.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

0.42 g of 7-cyano-7-(4,6-dimethoxypyrimidin-2-yl)-4-(2-furyl)furo[3,4-b]pyridin-5(7H)one was weighed out, and 14 ml of tetrahydrofuran was added thereto. The mixture was stirred under cooling with ice. 14 ml of 0.25N sodium hydroxide aqueous solution was added thereto dropwise, and the mixture was stirred at room temperature for 30 minutes. The mixture was poured into water, and the aqueous layer was washed with ethyl acetate twice, acidified with 10% hydrochloric acid and extracted with 100 ml of ethyl acetate. The extract was washed with saturated aqueous sodium chloride solution and then dried over anhydrous magnesium sulfate. The solvent was distilled off, and the resulting crystals were washed with methyl alcohol to obtain 0.40 g (yield 94.6%) of the desired compound as yellow crystals. m.p.: 198°-204° C.

Workup

  1. temperatureunder cooling with ice
  2. stirringdropwise, and the mixture was stirred at room temperature for 30 minutes
  3. washthe aqueous layer was washed with ethyl acetate twice
  4. extractionextracted with 100 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. washthe resulting crystals were washed with methyl alcohol

Sources & evidence

ORD record
ord-940d04a37e6f4e3f8e2ec65c0eb0cd63
Source dataset
uspto-grants-1999_03
Patent number
US05877120

Reaction notes

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