Pyruvic Acid → HCID 11740520, compound

HRID 1813919Notes

Reaction equation

HRID 1813919 reaction equation
[CH2:1]([CH:3]([O:6][C:7]1[N:12]=[C:11]([CH3:13])[N:10]=[C:9]([NH:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=2[CH3:23])[C:8]=1[NH2:24])[CH2:4][CH3:5])[CH3:2].[C:25](O)(=[O:29])[C:26]([CH3:28])=O>C(O)C>[CH2:1]([CH:3]([O:6][C:7]1[C:8]2[N:24]=[C:26]([CH3:28])[C:25](=[O:29])[N:14]([C:15]3[C:20]([CH3:21])=[CH:19][C:18]([CH3:22])=[CH:17][C:16]=3[CH3:23])[C:9]=2[N:10]=[C:11]([CH3:13])[N:12]=1)[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 2

HCID 1060Pyruvic Acid2×HCID 21912081HCID 21912081, compound

Product 1

HCID 11740520HCID 11740520, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6-(1-ethyl-propoxy)-2-methyl-4-N-(2,4,6-trimethyl-phenyl)-pyrimidine-4,5-diamine (100 mg, 0.305 mmol) in 2 ml of ethanol was added pyruvic acid (30 mg, 0.335 mmol) and the resulting mixture was heated at reflux for 1 hour. An additional 60 mg of pyruvic acid was added and the resulting mixture was heated at reflux overnight. The mixture was quenched with water and extracted with chloroform. The organic layer was washed with water and brine, dried over sodium sulfate, filtered and concentrated to give an oil residue. The residue was purified through silica gel column chromatography using hexane to 15% ethyl acetate in hexane as eluent to give the title compound as a yellow solid. 1H NMR (CDCl3) δ 6.99 (s,2H), 5.39(m,1H), 2.61(s,3H), 2.40(s,3H), 2.35(s,3H), 1.88(s,6H), 1.7-1.9(m,4H), 0.99(t,6H)ppm.

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1 hour
  3. temperaturethe resulting mixture was heated
  4. temperatureat reflux overnight
  5. customThe mixture was quenched with water
  6. extractionextracted with chloroform
  7. washThe organic layer was washed with water and brine
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give an oil residue
  12. customThe residue was purified through silica gel column chromatography

Sources & evidence

ORD record
ord-f983998c625b4ce89f7b7416e8cedcbe
Source dataset
uspto-grants-2005_04
Patent number
US06875769B2

Reaction notes

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