Sodium Hydroxide → HCID 58909200, compound

HRID 1295613Notes

Reaction equation

HRID 1295613 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[CH:15]=[CH:14][O:13][C:12]=1[NH:16][C:17](=O)[CH2:18][CH2:19][CH3:20])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)CO>[CH2:1]([N:8]1[C:9](=[O:10])[C:11]2[CH:15]=[CH:14][O:13][C:12]=2[N:16]=[C:17]1[CH2:18][CH2:19][CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58909201HCID 58909201, compound

Product 1

HCID 58909200HCID 58909200, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of N-benzyl-2-(butyrylamino)-3-furamide (1-2, 1 equiv) and sodium hydroxide (0.1 equiv) in ethylene glycol is heated at 130° C. for 5 h. The reaction mixture is allowed to cool, then partitioned between a half-saturated aqueous sodium chloride solution and ethyl acetate. The combined organic layers are dried over sodium sulfate and concentrated. The residue is purified by flash column (hexanes initially, grading to 100% ethyl acetate) to provide 3-benzyl-2-propylfuro[2,3-d]pyrimidin-4(3H)-one (1-3).

Workup

  1. temperatureto cool
  2. custompartitioned between a half-saturated aqueous sodium chloride solution and ethyl acetate
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue is purified by flash column (hexanes initially

Sources & evidence

ORD record
ord-26d96abbd1654d44b6d78cefdad46c82
Source dataset
uspto-grants-2007_07
Patent number
US07244723B2

Reaction notes

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