Ethyl bromopyruvate → HCID 136377293, compound

HRID 1409325Notes

Reaction equation

HRID 1409325 reaction equation
Br[CH2:2][C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH:10]1[CH:17]=[CH:16][C:14]([NH2:15])=[N:13][C:11]1=[O:12]>C(O)C>[O:12]=[C:11]1[N:13]2[CH:2]=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:15]=[C:14]2[CH:16]=[CH:17][NH:10]1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 178418229Cytosine

Product 1

HCID 136377293HCID 136377293, compoundYield 14.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl bromopyruvate (18.00 mmol, 3.51 g) was dissolved in ethanol (50 ml). Cytosine (18.00 mmol, 2 g) was added and the resulting mixture was refluxed for 5.5 h. The mixture was evaporated and DCM was added. The precipitate was filtered and washed with water. The filtrate was washed with NaHCO3, water and evaporated. The evaporation residue and the previously filtered precipitate were purified by flash chromatography and trituration from water, respectively. 0.526 g of the title compound was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.31 (t, 3H), 4.29 (q, 2H), 6.60 (d, 1H), 7.30-7.38 (m, 1H), 8.22 (s, 1H), 11.77 (bs, 1H).

Workup

  1. temperaturethe resulting mixture was refluxed for 5.5 h
  2. customThe mixture was evaporated
  3. additionDCM was added
  4. filtrationThe precipitate was filtered
  5. washwashed with water
  6. washThe filtrate was washed with NaHCO3, water
  7. customevaporated
  8. customThe evaporation residue and the previously filtered precipitate were purified by flash chromatography and trituration from water

Sources & evidence

ORD record
ord-7021ecf3e231461e810bd2620090c4c8
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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