Ethanol → HCID 11587404, compound

HRID 556418Notes

Reaction equation

HRID 556418 reaction equation
[C:1]([N:9]=C=O)(=[O:8])C1C=CC=CC=1.C(O[C:15]([C:17]1[O:32][C:20]2=[N:21][C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:23][C:24]([CH3:25])=[C:19]2[C:18]=1[NH2:33])=[O:16])C.CC[O-].[Na+].C(O)C>CC(C)=O.O>[CH3:25][C:24]1[C:19]2[C:18]3[NH:33][C:1](=[O:8])[NH:9][C:15](=[O:16])[C:17]=3[O:32][C:20]=2[N:21]=[C:22]([C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:23]=1

Participants

7

Reactant 4

HCID 702EthanolHCID 78210Benzoyl isocyanateHCID 2723922Sodium ethoxideHCID 9971786HCID 9971786, compound

Product 1

HCID 11587404HCID 11587404, compoundYield 85.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

1.0 g (6.8 mmol) benzoylisocyanate is added to 1.0 g (3.4 mmol) 3-amino-4-methyl-6-phenyl-furo[2,3-b]pyridine-2-carboxylic acid ethyl ester (described in Wagner G., Prantz J. Pharmazie 1990, 45, 213-214) in 20 ml absolute acetone and stirred at room temperature for 30 minutes. The solvent is removed and the precipitate precipitated after the addition of water is sucked off and dried. The resulting precipitate is refluxed with 0.46 g (6.8 mmol) NaOEt and 20 ml ethanol for 15 min. Then, 20 ml water is added, the precipitate is sucked off, washed with some ethanol and dried. 0.85 g (85%) 9-methyl-7-phenyl-pyrido[3′,2′:4,5]furo[3,2-d]pyrimidin-2,4-dione is obtained

Workup

  1. customThe solvent is removed
  2. customthe precipitate precipitated
  3. additionafter the addition of water
  4. customdried
  5. washwashed with some ethanol
  6. customdried

Sources & evidence

ORD record
ord-418873c7e0ca4778a6200c8c284dfb89
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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