Potassium Carbonate → Ethyl 3-acetyl-1,2,3,4-tetrahydro-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidinecarboxylate

HRID 64591Notes

Reaction equation

HRID 64591 reaction equation
[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[O:19]C(=O)C)[C:8]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:7]([CH3:28])[NH:6][C:5]1=[O:29])(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>C(O)C>[C:1]([N:4]1[CH:9]([C:10]2[CH:15]=[C:14]([N+:16]([O-:18])=[O:17])[CH:13]=[CH:12][C:11]=2[OH:19])[C:8]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:7]([CH3:28])[NH:6][C:5]1=[O:29])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 20236390Ethyl 3-acetyl-1,2,3,4-tetrahydro-4-(2-acetoxy-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidine carboxylate

Product 1

HCID 20236388Ethyl 3-acetyl-1,2,3,4-tetrahydro-4-(2-hydroxy-5-nitrophenyl)-6-methyl-2-oxo-5-pyrimidinecarboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of the Compound 1a (1.03 g) in ethanol (60 mL) at ambient temperature was added potassium carbonate (2.0 g). After stirring for 18 hours, to the reaction mixture was added saturated aqueous ammonium chloride. The reaction mixture was then extracted with methylene chloride and the combined organic extracts were dried over anhydrous sodium sulfate and filtered. The filtrate was concentrated in vacuo and the residue purified by flash chromatography on silica gel eluted with methanol:methylene chloride (3:97) to yield the desired product as a solid.

Workup

  1. extractionThe reaction mixture was then extracted with methylene chloride
  2. dry with materialthe combined organic extracts were dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customthe residue purified by flash chromatography on silica gel
  6. washeluted with methanol:methylene chloride (3:97)

Sources & evidence

ORD record
ord-67302bf687d1411993f63793eafa3376
Source dataset
uspto-grants-1986_09
Patent number
US04609494

Reaction notes

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