Ethyl bromopyruvate → HCID 12744617, compound

HRID 1409319Notes

Reaction equation

HRID 1409319 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([CH3:9])[N:3]=1.Br[CH2:11][C:12](=O)[C:13]([O:15][CH2:16][CH3:17])=[O:14]>C(O)C>[CH3:9][C:4]1[N:3]2[CH:11]=[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:1]=[C:2]2[CH:7]=[C:6]([CH3:8])[N:5]=1

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 680392,6-Dimethyl-4-aminopyrimidine

Product 1

HCID 12744617HCID 12744617, compoundYield 8.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

4-Amino-2,6-dimethylpyrimidine (16.24 mmol, 2 g) was mixed with ethanol (30 ml) and stirred well. Ethyl bromopyruvate (20.30 mmol, 3.96 g) was added in small portions. The resulting mixture was refluxed for 5.5 h and stirred at RT overnight. The solvent was evaporated, DCM was added and washed with Na2HCO3. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography and trituration from EtOAc/heptane, respectively. 0.287 g of the title product was obtained. 1H-NMR (400 MHz, DMSO-d6): δ 1.33 (t, 3H), 2.42 (d, 3H), 2.80 (s, 3H), 4.33 (q, 2H), 7.32 (s, 1H), 8.50 (d, 1H).

Workup

  1. temperatureThe resulting mixture was refluxed for 5.5 h
  2. stirringstirred at RT overnight
  3. customThe solvent was evaporated
  4. additionDCM was added
  5. washwashed with Na2HCO3
  6. customThe organic phase was dried
  7. filtrationfiltered
  8. customevaporated
  9. customThe crude product was purified by flash chromatography and trituration from EtOAc/heptane

Sources & evidence

ORD record
ord-7af57124113640a09642e6c5aafffb72
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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