Acetic Anhydride → HCID 53298866, compound

HRID 131289Notes

Reaction equation

HRID 131289 reaction equation
C(OC(=O)C)(=[O:3])C.[C:8]([C:10]1[C:14]([CH3:15])=[C:13]([CH3:16])[O:12][C:11]=1[NH:17][C:18](=O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])#[N:9]>C(O)=O>[CH3:15][C:14]1[C:10]2[C:8](=[O:3])[NH:9][C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[N:17][C:11]=2[O:12][C:13]=1[CH3:16]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 319447ethyl [(3-cyano-4,5-dimethylfuran-2-yl)amino](oxo)acetate

Product 1

HCID 53298866HCID 53298866, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 284Formic AcidSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of the compound obtained in the above step (1) (13.6 g) in methylene chloride (200 mL) is added piperidine (18.9 g) and thereto is added dropwise a solution of ethyl chlorooxoacetate (16.3 g) in methylene chlorode (200 mL) under ice-cooling. The mixture is stirred at 0° C. for 1.5 hours. The reaction mixture is diluted with chloroform (100 mL) and thereto is added water (300 mL). After stirring, the organic layer is separated and the aqueous layer is extracted with chloroform. The organic layers are combined and washed with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate is concentrated and the residue is purified by column chromatography on silica gel (Solvent; chloroform:ethyl acetate=9:1) to give ethyl [(3-cyano-4,5-dimethylfuran-2-yl)amino](oxo)acetate (17 g, yield; 72%) as a colorless powder. A mixture of formic acid (30 mL) and acetic anhydride (30 mL) is stirred at 60° C. under argon gas atmosphere for 2 hours and thereto is added ethyl [(3-cyano-4,5-dimethylfuran-2-yl)amino](oxo)acetate (7.07 g). The mixture is refluxed for 14 hours. The reaction mixture is concentrated and the residue is purified by column chromatography on silica gel (Solvent; chloroform:ethyl acetate=9:1→chloroform:methanol=19:1) to give ethyl 5,6-dimethyl-4-oxo-3,4-dihydrofuro[2,3-d]pyrimidine-2-carboxylate (4.30 g, yield; 61%) as a colorless powder. M.p. 180-182° C.

Workup

  1. temperatureThe mixture is refluxed for 14 hours
  2. concentrationThe reaction mixture is concentrated
  3. customthe residue is purified by column chromatography on silica gel (Solvent; chloroform:ethyl acetate=9:1→chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-3b371498d6ba47cc9764a71fafdf168b
Source dataset
uspto-grants-2008_06
Patent number
US07384952B2

Reaction notes

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