Triethylamine → HCID 59509029, compound

HRID 1020075Notes

Reaction equation

HRID 1020075 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=1.CCN(CC)CC.[CH3:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26]>C1COCC1.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[N:14]=[CH:13][N:12]=[C:11]([NH:15][C:25](=[O:26])[C:24]([CH3:29])([CH3:28])[CH3:23])[CH:10]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 497584396-(2-Methoxyphenyl)pyrimidin-4-amine

Product 1

HCID 59509029HCID 59509029, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-(2-methoxy-phenyl)-pyrimidin-4-ylamine (XXIV) (0.15 g, 0.74 mmol) in THF (10 ml) was added NEt3 (0.210 ml, 1.49 mmol) under an atmosphere of nitrogen at ice bath temperature, followed by trimethyl acetyl chloride (XLV) (0.819 mmol) at the same temperature. The reaction mixture was stirred for 1 hour at 0° C., then it was brought to room temperature and stirred for another hour. After completion of the reaction, the solvent was removed under reduced pressure. The crude reaction product was taken in ethyl acetate (50 ml) and washed with water (2×20 ml). The organic layer was separated, washed with brine, dried over anhydrous sodium sulfate and concentrated to dryness at reduced pressure to give crude product which was further purified by column chromatography over silica gel (20% ethylacetate/hexane) to yield N-[6-(2-methoxy-phenyl)-pyrimidin-4-yl]-2,2-dimethyl-propionamide. Yield: 106 mg, 50%.

Workup

  1. customwas brought to room temperature
  2. stirringstirred for another hour
  3. customAfter completion of the reaction
  4. customthe solvent was removed under reduced pressure
  5. customThe crude reaction product
  6. washwashed with water (2×20 ml)
  7. customThe organic layer was separated
  8. washwashed with brine
  9. dry with materialdried over anhydrous sodium sulfate
  10. concentrationconcentrated to dryness at reduced pressure
  11. customto give crude product which
  12. customwas further purified by column chromatography over silica gel (20% ethylacetate/hexane)

Sources & evidence

ORD record
ord-c45267d414094e3abc25f9c95600f7ff
Source dataset
uspto-grants-2014_05
Patent number
US08716296B2

Reaction notes

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