Triethylamine → HCID 58826030, compound

HRID 1714852Notes

Reaction equation

HRID 1714852 reaction equation
[NH2:1][C:2]1[C:7]([O:8][C:9]2[CH:14]=[C:13]([I:15])[C:12]([O:16][CH3:17])=[CH:11][C:10]=2[CH:18]([CH3:20])[CH3:19])=[CH:6][N:5]=[C:4]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])[N:3]=1.C(N(CC)CC)C.[C:34](Cl)(=[O:38])[CH:35]([CH3:37])[CH3:36]>O1CCCC1>[I:15][C:13]1[C:12]([O:16][CH3:17])=[CH:11][C:10]([CH:18]([CH3:20])[CH3:19])=[C:9]([CH:14]=1)[O:8][C:7]1[C:2]([NH:1][C:34](=[O:38])[CH:35]([CH3:37])[CH3:36])=[N:3][C:4]([NH:21][C:22](=[O:26])[CH:23]([CH3:25])[CH3:24])=[N:5][CH:6]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62325Isobutyryl chlorideHCID 15953858HCID 15953858, compound

Product 1

HCID 58826030HCID 58826030, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To N-[4-amino-5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-pyrimidin-2-yl]-isobutyramide (386 mg, 0.82 mmol), dissolved in anhydrous tetrahydrofuran, was added triethylamine (0.13 mL, 0.90 mmol) and isobutyryl chloride (0.09 mL, 0.90 mmol). After stirring one hour, the reaction was concentrated under reduced pressure. The concentrate was dissolved in dichloromethane (50 mL), and the dichloromethane layer was washed with water, dried using anhydrous sodium sulfate, and concentrated under reduced pressure. Purification by preparatory TLC plates (98/2/0.5 dichloromethane/methanol/ammonium hydroxide) yielded 96 mg (22%) of N-[5-(5-iodo-2-isopropyl-4-methoxy-phenoxy)-4-isobutyrylamino-pyrimidin-2-yl]-isobutyramide as white solid, MS (M+H)=541.

Workup

  1. concentrationthe reaction was concentrated under reduced pressure
  2. dissolutionThe concentrate was dissolved in dichloromethane (50 mL)
  3. washthe dichloromethane layer was washed with water
  4. customdried
  5. concentrationconcentrated under reduced pressure
  6. customPurification by preparatory TLC plates (98/2/0.5 dichloromethane/methanol/ammonium hydroxide)

Sources & evidence

ORD record
ord-690b5351a9284a559c2bcf16c2f651f8
Source dataset
uspto-grants-2010_09
Patent number
US07799796B2

Reaction notes

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